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Aminobenzophenone

A solution of 2-aminobenzophenone (98 g, 0.50 mol) and methyl 2-(methyl-thio)propanoate (74 g, 0,50 mol) in CH Clj (21) was cooled to —70 C and 95% 7-butyl hypochlorite (56 g, 0.5 mol) was added dropwise at such a rate that the temperature did not rise above — 65 C. One hour after the addition was complete, EtjN was added and the mixture was allowed to come to room temperature. The solution w as mixed with 3 N HCl (800 ml) and stirred for 1 h. The organic layer was separated, dried (Na2S04 ) and filtered. The solution was evaporated in vacuo and the residue triturated with ether. Filtration gave the 3-(methylthio)oxindole intermediate (92 g) in 62% yield. [Pg.73]

Aminobenzophenone Glycine ethyl ester hydrochloride Nitric acid... [Pg.1087]

A mixture of 16.8 g of 2-aminobenzophenone, 11.9 g of glycine ethyl ester hydrochloride and 200 cc of pyridine was heated to reflux. After one hour, 20 cc of pyridine was distilled off. The solution was refluxed for 15 hours, then 11.9 g of glycine ethyl ester hydrochloride was added and the refluxing was continued for an additional 4 hours. The reaction mixture was continued for an additional 4 hours. The reaction mixture was concentrated in vacuo, then diluted with ether and water. The reaction product, 5-phenyl-3H-1,4-benzodiazepin-2(1 H)-one, crystallized out, was filtered off, and then recrystallized from acetone in the form of colorless rhombic prisms, MP 182°Cto 183°C. [Pg.1087]

The action of a-amino acid ethyl ester hydrochlorides on 2-aminobenzophenones in hot pyridine gives benzodiazepinones 4 directly (Method A). Selected examples are given.193194... [Pg.390]

A solution of a 2-aminobenzophenone (0.1 mol) and an z-amino acid ethyl ester hydrochloride (0.15 mol) in pyridine (200 mL) was refluxed. During the first 4h, 20-50 mL of liquid was allowed to distill and was replaced by fresh pyridine. Heating was continued for a further 11 h, the mixture was evaporated under reduced pressure and H20 and Et20 were added. In most cases some of the reaction product remained undissolved and was filtered off. The aqueous layer was separated, made alkaline and extracted with Et20. The comhined F.t20 phases were washed with H20. dried and evaporated and the reaction product was separated from unchanged amino ketone by crystallization. [Pg.391]

A three-stage procedure is more versatile and gives higher yields. In this method (Method B), the 2-aminobenzophenone is treated with an a-haloacetyl halide and the resulting haloacetamide 5 converted into an aminoacetamide 6 by reaction with ammonia. Cyclization to the benzo-diazepinone 7 occurrs readily. In some cases the intermediates 5 and 6 are not isolated selected examples are given.193 94... [Pg.391]

Ice (500 g) and hromoacetyl bromide (26.3 g, 0.13 mol) were added simultaneously in portions to a stirred solution of a 2-aminobenzophenone (0.1 mol) in Et20 (500 mL) at such a rate that the temperature remained at 10-15 C. After 1 — 2 h the Et,0 layer was separated, washed with H20, followed by dil aq NaOH, dried (Na2S04) and evaporated under reduced pressure to give 5. [Pg.391]

A further variant of Method B is the acylation of a 2-aminobenzophenone with a protected a-amino acid chloride, followed by conversion of the product 11 into the 2-(aminoacet-amido)benzophenone 12 by reaction with hydrobromic acid in acetic acid.196... [Pg.392]

In another procedure, 2-aminobenzophenone is acylated with an sc-azido acid in the presence of l-[3-(dimethylamino)propyl]-3-ethylcarbodiimide and the product 23 is converted into a benzodiazepinone by reductive cyclization with propane-1,3-dithiol (Method F).200... [Pg.394]

Hydrobromides 13 of 3//-1,3,4-benzotriazepin-2-amines are formed in the reaction of 2-aminobenzophenone hydrazones 12 with cyanogen bromide. Selected examples are given.356... [Pg.464]

Aminobenzophenone (19.7 g, 0.1 mol) was dissolved in chlorobenzene (250 mL), A1C13 (7.5 g, 56 mmol) was added, and the solution was heated under reflux for 8 h. After cooling, the solution was washed with aq NaOH, and the solvent was removed in vacuo. Recrystallization (CH2Cl2/EtOH) gave pale-yellow prisms yield 12.7 g (71%) mp 191-193 C. [Pg.543]

The oxo function in the 2-aminobenzophenone can also be masked as an imino function,31 32 an example being the reaction of 10. [Pg.543]

Syntheses starting from amides of 2-aminobenzoic acid and 2-aminobenzophenone derivatives are also known.34,35... [Pg.543]

Aminobenzophenone, 32, 8 c-Aminocaproic acid, 32, 13 6-Aminocaproic acid hydrochloride, 32, 13... [Pg.52]

Methoxyphenylurea, 31,10,13 Methyl -acetylbenzoate, 32, 81 Methyl acrylate, 30, 65 32, 86 y-Methylallophanate, 32, 62 Methylamine, 30, 60 4 -Methyl-2-aminobenzophenone, 32,12 N-Methylaniline, 30, 62 31,110 N-Methylarylamines, preparation by reductive alkylation, 30, 59, 60 Methylation, of e-caprolactam, 31, 72 of quinacetophenone, with dimethyl sulfate, 31, 91 with methyl iodide, 31, 90 2-Methyl-3,l,4-benzoxaz-4-one, 32, 12 N-Methyl-a-bromo-n-butyranilide, 30, 63... [Pg.56]

In a further exploration of the relationship between dye structure and wet fastness on silk, four novel monoazo J acid derivatives (3.169 X = Xx to X4), including 3.168 (X = X2) made from 2-aminobenzophenone, were synthesised. Silk was dyed at pH 4 and 85 °C and the dyeings tested for fastness to washing, perspiration and dry cleaning. The highest allround fastness was shown by the 4 aminobenzophenone derivative (X = X4), a structure that resembles the anti-parallel pleated sheet arrangement of polypeptide chains in silk [183]. [Pg.168]

Determination of halogenated 2-aminobenzophenones (64a-c), which are metabolites of psychotropic drugs, was performed by HPLC with amperometric detection (GCE vs Ag/AgCl) LOQ 750 ng of metabolite/L of biological fluid (urine or serum), with recovery better than 97%183. [Pg.1074]

Reaction of 2-aminobenzophenone with acetyl acetone in the presence of Bi(OTf)3 (5 mol%) results in the formation of 3-acetyl-2-methyl-4-phenylquinoline [117]. Various 1,3-diketones, acyclic ketones and cyclic ketone undergo the condensation with 2-aminoaryl ketones. The scope and generality of this process is illustrated with respect to various 2-aminoaryl ketones and a wide array of a-methylene ketones, and the results are summarized in Table 6. This method is free from side reactions such as the self-condensation of ketones, which is normally observed under basic conditions. Unlike reported methods, the present protocol does not require high temperature or drastic conditions to produce quinoline derivatives. [Pg.252]

Aldehydes have also been condensed with 2-aminobenzophenone oximes 811, but in this case an added oxidant is not needed, as loss of water from the iV-oxide intermediate 812 provides 2-substituted -phenylquinazolines 813 directly <2004AP239>. [Pg.211]

The reaction of 2-imino-2/7-pyrano[2,3-c]pyridine-3-carboxamide with substituted 2-aminobenzophenones proceeds via ring opening and recyclization to give 3-(4-arylquinazolyn-2-yl)-277-pyrano[2,3-( ]pyridin-2-ones (Scheme 9) <2005SG1641>. [Pg.719]

There is obtained 257-265 g. (88-91%) of />-toluenesulfonylan-t hranilic acid as a pale lavender powder with a neutral equivalent of 294-300, which indicates a purity of 97-99% (Note 3). This product is suitable for conversion to 2-aminobenzophenone, but it may be recrystallized by dissolving in hot 95% ethanol (10 ml. per g.) and then adding water (4 ml. per g.). The recovery in the first crop is about 75% of material melting at 229-230° and having a neutral equivalent of 295. [Pg.9]

If sodium hydroxide is used, the main product is the />-tolu-enesulfonic acid salt of anthranilic acid. This salt has properties quite similar to those of the desired />-toluen esulfonylanthranilic acid but is useless for the preparation of 2-aminobenzophenone. [Pg.11]

When recrystallized -toluenesulfonylanthranilic acid is used, the solution is clear at this point. The crude acid gives rise to a dark solution containing a small amount of suspended solid. The yield of 2-aminobenzophenone is the same in either case. [Pg.11]

Methyl-2-aminobenzophenone can be prepared similarly by substituting toluene for benzene. The yield of crude material, m.p. 85-88°, is 70%. On recrystallization from 95% ethanol, using 5 ml. per g., there is obtained, in two crops, a 70% recovery of 4/-methyl-2-aminobenzophenone, m.p. 92-93°. Because of the higher temperature required in the steam distillation (cf. Note 5), the sulfonamide is obtained in a form difficult to purify. As a result the crude aminoketone usually contains 1-2 g. of aluminum oxide. [Pg.12]

The above procedure is essentially that of Ullmann and Bleier.2 2-Aminobenzophenone has also been prepared by reduction of 2-nitrobenzophenone,3 by the Hofmann reaction of the amide of o-benzoylbenzoic acid with sodium hypobromite,4 by the action of an excess of benzoyl chloride on aniline at 220°,6 and by hydrolysis of the acetyl derivative which is obtained by the action of phenylmagnesium bromide on 2-methyl-3,l,4-benzoxaz-4-one (from anthranilic acid and acetic anhydride).6 Various methods for the preparation of 2-aminobenzophenones have been summarized critically by Simpson, Atkinson, Schofield, and Stephenson.7... [Pg.12]

The first starting material for building benzodiazepines was prepared inadvertently in a synthesis aimed at the benzodiazoxepine (6-1). The oxime acetamide (6-2) from 2-aminobenzophenone was thus treated with hydrogen chloride in the expectation that the new heterocycle would form by the elimination of water between the oxime and the enol form of the amide. The product mrned out in fact to be the quinazoline A-oxide (6-3), the product from the addition of the nucleophilic oxime nitrogen to the amide carbonyl group. [Pg.500]

Preparative routes to 5/7-dibenz[6,e]azepine-6,11 -diones (morphanthridinediones) are based mainly on the cyclization of 2-aminobenzophenone-2 -carboxylic acids and their derivatives (55LA(594)89). Studies on a-aminodiphenyImethane-2 -carboxylic acid reveal that cyclization to 5,11 -dibenz[6,e ]azepinone (188) is much slower at room temperature than the cyclizations of the analogous 2-aminobiphenyl-2 -carboxylic acid and the 2 -aminobiphenylacetic acid (189), which at room temperature cyclize spontaneously to phenanthridone and dibenz[f>,d]azepin-6-one (190) respectively (61JOC1329). The hydrogen bromide-induced cyclization of dinitriles (Scheme 16) is adaptable to the synthesis of 2-amino-7-bromo-3//-azepines and 5H-dibenz[c,e]azepin-7-ones (67JOC3325). Apparently, for unsymmetrical dinitriles cyclization is such as always to give the azepine with the bromo substituent attached to the carbon of the a,j8-unsaturated nitrile as exemplified in Scheme 16. [Pg.529]

Amide reduction with lithium aluminum hydride, 39, 19 Amine oxide formation, 39, 40 Amine oxide pyrolysis, 39, 41, 42 -Aminoacetanilide, 39, 1 Amino adds, synthesis of, 30, 7 2-Amino-4-anilino-6-(chloro-METHYl) -S-TRIAZINE, 38, 1 -Aminobenzaldehyde, 31, 6 hydrazone, 31, 7 oxime, 31, 7 phenylhydrazone, 31, 7 > -Aminobenzoic add, 36, 95 2-Aminobenzophenone, 32, 8 c-Aminocaproic acid, 32, 13 6-Aminocaproic acid hydrochloride,... [Pg.83]


See other pages where Aminobenzophenone is mentioned: [Pg.1612]    [Pg.1451]    [Pg.2346]    [Pg.84]    [Pg.44]    [Pg.59]    [Pg.75]    [Pg.53]    [Pg.130]    [Pg.177]    [Pg.624]    [Pg.1338]    [Pg.9]    [Pg.11]    [Pg.11]    [Pg.609]   
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See also in sourсe #XX -- [ Pg.8 , Pg.32 ]

See also in sourсe #XX -- [ Pg.8 , Pg.32 ]

See also in sourсe #XX -- [ Pg.8 , Pg.32 ]

See also in sourсe #XX -- [ Pg.8 , Pg.32 ]

See also in sourсe #XX -- [ Pg.1181 ]

See also in sourсe #XX -- [ Pg.27 , Pg.43 ]

See also in sourсe #XX -- [ Pg.8 , Pg.32 ]

See also in sourсe #XX -- [ Pg.8 , Pg.32 ]




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2-Aminobenzophenone Aminocaproic acid

2-Aminobenzophenone, condensation with

3-Aminobenzophenone compounds

4 -Methyl-2-aminobenzophenone

Aminobenzophenones

O-Aminobenzophenone

O-Aminobenzophenones

Ortho-Aminobenzophenones

Ortho-aminobenzophenone

P- Aminobenzophenone

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