Hydroxyl amine.hydrochloride

An assay method for benzaldehyde involves condensing benzaldehyde with hydroxyl amine hydrochloride to form an oxime. The released hydrochloric acid is then titrated. 

Carbonyl-containing and unsaturated materials are removed by treatment with sodium borohydride (227,228) and boric acid (229). Other methods used to remove carbonyl impurities include treatment with hydroxyl amine hydrochloride, potassium permanganate, or A/-hydroxyben2enesulfonamide (229). 

Chloroaeetophenone oxime was prepared by a modification of the method described by Shriner, Fuson, and Curtin.5 A mixture of 100 g. (0.65 mole) of reagent-grade 4-chloroacetophenone, 300 ml. of water, 200 ml. of aqueous 10% sodium hydroxide, 50g. (0.72 mole) of hydroxyl-amine hydrochloride, and 500 ml. of ethanol is heated at reflux in a 2-1. round-bottomed flask for 2 hours. The crystals that separate on cooling in an ice bath are recovered by filtration and air dried. The product is added to approximately 1 1. of hexane, and the mixture is... 

Benzophenoneoxime has been prepared in quantity by treating an aqueous alcoholic mixture of benzophenone and hydroxyl-amine hydrochloride with hydrochloric acid,2 with sodium carbonate,3 with alcoholic potassium hydroxide,4 or with aqueous sodium hydroxide. It has also been obtained by treating bis-nitrosylbenzohydryl with alcoholic potassium hydroxide,6 and by the oxidation of a-aminodiphenylmethane with magnesium persulfate solution.7... 

Nitroso-/3-naphthol has been made by the action of hydroxyl-amine hydrochloride on /3-naphtho-quinonc-chlorimide 1 by the action of sulfuric acid upon a solution of potassium or sodium nitrite and the sodium salt of /3-naphthol 2 by the action of sodium nitrite upon an alcoholic solution of zinc chloride and /3-naphthol 3 by the action of sodium nitrite upon /3-naphthol suspended in zinc sulfate solution 4 by the action of nitrous acid on /3-dinaphthol methane 6 and by the action of nitrosyl sulfate upon the sodium salt of /3-naphthol.6... 

The reaction of diethyl acetyl- and propionylmalonates with hydroxyl-amine hydrochloride or its N-methyl derivative in ethanol afforded the appropriate ethyl 3-alkyl-2,5-dihydro-5-oxo-4-isoxazolecarboxylate (88-TL6339). 

The reactivity of the keto group is not influenced by the substitution the reaction of 3-(trifluoromethylmercapto)-2-butanone with hydroxyl-amine hydrochloride gives the corresponding oxime in good yield. Cyclization of diketones and keto esters to pyrazole derivatives succeeds by the well-known method using phenylhydrazine ... 

Pure nitrous oxide may be prepared by treating a solution of sodium nitrite, NaN02 with that of hydroxyl amine hydrochloride, NH20H HC1 ... 

Werden Thiokohlensaure-(ethoxycarbonyl-amide) nach obigen Bedingungen mit Hydroxyl-amin-Hydrochlorid und Natriumacetat in Ethanol umgesetzt, so erhalt man unter Ethanol-Abspaltung 5-Hydroxy-l, 2,4-oxadiazole182. 

The acetoxime may be distilled by direct heating rather than by injection of steam when the prescribed quantities are taken, however, it will be found that the liquor becomes saturated with sodium sulfate at a point just before the expulsion of the oxime is complete, so that addition of water during the distillation is necessary. More rapid distillation can be obtained by the use of a current of steam, especially if a condensing receiver (Vol. II, pp. 80-82) be employed. The oxime can also, if desired, be isolated for hydrolysis by separation of the oily layer and extraction with benzene the resulting crude hydroxyl-amine hydrochloride is, however apt to be dark in color and to contain inorganic salts. 

Trihydroxylamino-manganous Carbonate, [Mn(NH20H)3]C03. 2HaO, is produced as a white or grey powder when a solution of sodium carbonate and hydroxyl amine hydrochloride is added to an aqueous solution of manganous chloride.9... 

Fig. 3.1.9 Mass spectra of succinylacetone. a,b Peaks I and II, with oximation (reagent hydroxyl-amine hydrochloride). The insert shows the characteristic appearance of the two chromatographic peaks [32] c-e see next page...

A modified synthesis of vardenafil (2) on a multi-kilogram scale has recently been reported by a group from Bayer (Scheme 4). Benzamidine 12 was prepared in a different manner than described in Scheme 3, because it is difficult to use trimethylaluminium on a large scale. Thus, 2-ethoxybenzamide was dehydrated with thionyl chloride to give 2-ethoxybenzonitrile, which was treated with hydroxyl amine hydrochloride to afford the /V-hydroxybenzamidine 19. Catalytic hydrogenation of 19... 

A. 4-Aaetylpyridine oxime. Hydroxyl amine hydrochloride (25.0 g, 0.36 mol) (Note 1) is dissolved in 50 mL of water, and the solution 1s added to 70 mL of 20K aqueous sodium hydroxide in a 500-mL Erlenmeyer flask. To this magnetically stirred solution 1s added at one time 4-acetyl pyridine (36.3 g, 0.30 mol) (Note 2) a precipitate forms rapidly. The reaction mixture is stirred at 0-5°C for 2 hr then the precipitate is collected by suction filtration and washed with 500 mL of cold water. 

Hydroxyl amine hydrochloride 97% (mp 155-157°C), available from Aldrich Chemical Company, Inc. or Fisher Scientific Company, is suitable for use without further purification. 

Hydroxylamine hydrochloride (8) Hydroxyl amine, hydrochloride (9) (5470-11-1) 4-Acetyl pyridine oxime Ketone, methyl 4-pyridyl oxime (8) Ethanone, l-(4-pyridinyl)- oxime (9) (1194-99-6)... 

Acetoxime, A zl do Derivative (Azido acetoxime, Triazo acetoxime or 1-Azi do-2-prop aneoxime), CH,. C( NOH). CH,. N mw] 14.11, N49-10%. Col oil, bp 84° at 2 mm with partial decompn. Was prepd from azidoacetone and hydroxyl-amine hydrochloride in aq soln contg some soda ash. When an attempt was made to distil 50g of azidoacetoxime at 2 mm, about 25 g distilled off at 84° while the residue in the flask gradually darkened and then violently exploded... 

Secondly, ammonium bromoselenate was reduced with hydroxyl-amine hydrochloride and the resulting selenium weighed ... 

Quantitative Determination. — Dissolve 1 gm. of hydroxyl-amine hydrochloride in 30 cc. of water, and titrate the solution with normal potassium hydroxide to permanent redness, using plienolphthalein as indicator. 

Other methods for the determination of aldehydes and ketones are those of Bene-dikt and Strache (carbonyl number), Hanus (phenylhydrazine), and Bennett (hydroxyl-amine hydrochloride). See Charabot, Dupont et Pillet Les Huiles essentielles, 1899. 

Seventy grams (1.0 mol) of dry finely powdered hydroxyl-amine hydrochloride and 0.01 to 0.02 g. of solid phenol-phthalein are placed in the flask. One hundred milliliters of butyl alcohol is added and after 10 minutes of preliminary stirring, the butoxide solution is introduced at such a rate that the pink color of the indicator never predominates. After about 2.5 hours, the end point of the reaction is just exceeded. To discharge the pink color, a small quantity of hydroxylamine hydrochloride is introduced in the flask, and stirring is continued until the solution becomes colorless. 

Treatment of 4-dimethylaminomethylene-2//-thiopyran-3,5(4//,6//)-dione (575) with hydroxyl-amine hydrochloride in refluxing MeOH gives compound (576) in good yield (Equation (56)) (84JHC1437). 

The A-oxide (144) was transformed by NaOH into the oxadiazole (148), accompanied by minor amounts of compounds (146) and (147), whereas the A-oxide (145) gave compound (146). Hydroxyl-amine hydrochloride converted (145) to compound (149). Treatment of the A-oxide (144) with nitrous acid yielded a substituted nicotinamide <87M399>. 

Benzotellurazole1 14.3 g (50 mmol) of 2-formylphenyl butyl tellurium, 3.8 g (55 mmol) of hydroxyl-amine hydrochloride, and 5.9 g (60 mmol) of fused potassium acetate are added to 100 ml of absolute ethanol and the mixture is heated under reflux with stirring for 2 h. The mixture is then concentrated, extracted with chloroform, and the extract is concentrated. The residue (the crude oxime) is added to a mixture of 50 ml of 85% phosphoric acid and 100 g of phosphorus pentoxide. This mixture is stirred and heated at 100° for 1 h, cooled, and poured into a mixture of ice and aqueous ammonia. The mixture is filtered, the solid is extracted with chloroform and the extract is dried and evaporated. The residue is recrystallized from methanol yield 4.6 g (40%) m.p. 173. ... 

Apparatus Use a 40- x 2.5-cm (id) glass column packed with Celite (Johns Mansville No. 595, or equivalent) prepared as described under Procedure. Dissolve 20 g of hydroxyl-amine hydrochloride in 500 mL of water, place the solution into a 2-L separatory funnel, and add 450 mL of butanol, 450 mL of chloroform, 300 mL of water, and 100 mL of hydrochloric acid. Agitate the mixture well, periodically venting the funnel. After settling, separate and store the bottom layer (organic), the Mobile Phase, and the top layer (aqueous), the Stationary Phase. 

The Se70° which is grown from As70 is separated by di-rect pptn. from HC1 soln. by addition of solid hydroxyl-amine hydrochloride. 

Step 1. Extraction of the acid soluble fraction (i.e., carbonates) with CH3COOH Step 2. Extraction of the reducible fraction (i.e., iron/manganese oxides) with hydroxyl amine hydrochloride... 

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