Acetonitrile phenyl

In the 3-adrenergic blocking drug pyrroxan (48), the catechol moiety is masked in a doxane ring. The synthesis begins by alkylation of phenyl acetonitrile by 2-chloroethanol to produce alcohol Recuction converts this to amino alcohol which... 

The separated oil is taken up in ether. After drying the ethereal solution over sodium sulfate and distilling off the ether, the resulting crude o -isopropyl-a-(/3 -dimethylamino propyl) phenyl acetonitrile is purified by distillation in a vacuum. The compound boils at 138° to 146°C/3 mm, according to U.S. Patent 2,934,557. 

As described in U.S. Patent 2,507,631, 80 g of pulverized sodium amide are gradually added, while stirring and cooling, to a solution of 117 g of phenyl-acetonitrile and 113 g of 2-chloropyridine in 400 cc of absolute toluene. The mixture is then slowly heated to 110° to 120°C and maintained at this temperature for 1 hour. Water is added thereto after cooling, the toluene solution is shaken with dilute hydrochloric acid and the hydrochloric acid extracts are made alkaline with concentrated caustic soda solution. A solid mass is separated thereby which is taken up in acetic ester and distilled, a-phenyl-a-pvridyl-(2)-acetonitrile passing over at 150° to 155°C under 0.5 mm pressure. When re-crystallized from ethyl acetate it melts at 88° to 89°C, the yield amounting to 135 g. 

Ooct-OPV3-CN was synthesized front (4-cyanomcthyI-2,5-bis( -oclyIoxy)phcn-yI)acetonitrile and benzaldehyde. Ooct-OPV5-CN was synthesized as depicted in Figure 16-8 front (4-cyanomethyI-2,5-bis(/i-octyIoxy)phenyl)acetonitrile and4-styr-ylbcnzaldehyde. 

Es kann ferner von Phenyl-acetonitril, Cyanessigsaure-athylester und Acrylsaure-nitril ausgegangen werden. lm letzteren Fall wird die Homologisierung durch Michael-Addition eincr C—H-aciden Verbindung an das erhal-tene 4,4,6-Trimethyl-2-vinyl-5,6-dihydro-4H-l,3-oxazin durchgefiihrt1. 

S)-0-P-D-Glucopyranosylmandelonitrile or (S)-(p-D-glucopyranosyloxy)(phenyl)acetonitrile trivial name sambunigrin... 

The reactions were carried out with 0.010 mole of the amino acid, 0.011 mole of 2-[Pg.186]

When piperidone 60 is condensed with phenyl-acetonitrile, using sodium methoxide, 84 results. Catalytic reduction unexpectedly is nonselective, not only reducing the olefinic linkage, but also removing... 

I.3.4.2.5. Carbonyl and Thiocarbonyl Compounds a-(Hydroxyimino)phenyl-acetonitrile oxide (generated in situ at room temperature from PhC( NOH)C ( NOH)Cl in the presence of NaHC03 or Et3N) reacts with simple aldehydes and ketones R1R2CO to give 1,4,2-dioxazoles 180 (347). Related dioxazoles, formed by cycloaddition of benzonitrile oxide to aromatic aldehydes, upon treatment with I-BuOK, undergo cyclo-reversion, allowing direct conversion to substituted benzoic acids or their esters (348). 

Quaternary ammonium salts are generally stable under neutral or acidic conditions up to 150°C, but decomposition can occur with the quaternary ammonium ion acting as an alkylating agent in its reaction with anions (Scheme 1.1). Soft nucleophiles, such as RS, are more reactive with tetra-n-butylammonium bromide and benzyltriethylammonium chloride, although the latter salt also C-benzylates phenyl-acetonitrile under basic conditions [46], These side reactions are considerably slower than the main catalysed reactions with, for example, a haloalkane and the amount of unwanted impurity in the final alkylated product is never greater than the amount of catalyst used (i.e. generally > 2%). Harder anions, e.g. R2N and RO, rarely react with the ammonium salts. 

Castro (1964) reported that iron(II) porphyrins in dilute aqueous solution was rapidly oxidized by DDT to form the corresponding iron(III) chloride complex (hematin) and DDE, respectively. Incubation of /5,//-DDT with hematin and ammonia gave p./Z-DDD, p./Z-DDE, bis(/5-chloro-phenyl)acetonitrile, l-chloro-2,2-bis(jD-chlorophenyl)ethylene, 4,4 -dichlorobenzophenone, and the methyl ester of bis (jo-chlorophenyl) acetic acid (Quirke et al., 1979). 

Photolysis and p5Tolysis of 4-phenyltriazole gives mainly phenyl-acetonitrile pyrolysis of 4,5-diphenyltriazole in solution gives 2,3,5,6-tetraphenylpyrazine, which is formally derived from the triazole by loss of nitrogen, dimerization, and oxidation (Scheme 58). ... 

This strategy also provides a convenient method for amination of various ester enolates with DPH Ih (Scheme 14). The amination of lithium eniminate of phenyl acetonitrile, the silyl enolate of ethyl phenylacetate and the Reformatsky reagent derived from ethyl a-bromoacetate with DPH were found to be unsuccessful. A failure of DPH for the amination of sodium enolates of S-diketones and the lithium enolate of 3-methylbutanoic acid was also reported . 

Die Kondensation von 2-Amino-2-phenyl- bzw. 2-Methylamino-2-phenyl-acetonitril mit Benz-aldehyd in Diethylether unter Katalyse mit Chlorwasserstoff liefert 2,4(5)-Diphenyl- (65%) bzw. 2,5-Diphenyl-l-methyHmidazol (76%)278,279 ... 

Das aus Phenyl-glyoxal-bis-oxim mit einem Aquivalent Acetanhydrid zugangliche 3-Phenyl-furazan (87%)318 wird in heiflem Acetanhydrid zu Acetoximino-phenyl-acetonitril umgesetzt318 ... 

Die Photolyse von 4-Azido-3-phenyl-furazan-2-oxid in Dichlormethan/Ethanol fiihrt in einer stereoselektiven Reaktion zum (thermodynamisch weniger stabilen) (E)-2-Hydroximino-2-phenyl-acetonitril, bei der Pyrolyse (in Pentanol) entstehen sowohl das (E)- als auch das (Z)-Oxim426. 

HCOONHVPd-C/CHjOH (trocken) 20 25° 2 h NaH4 H20/Pd —C/C2HsOH 20-25° bis zutn Verschwinden der Trlibung ( 4- Amino-phenyl)-acetonitril ( 4-Amino-phenyl)-acetonitril 85 100 3 9... 

The above method has been used in the preparation of other ring-substituted diphenylacetoacetonitriles. The method is equally successful when applied to the condensation of phenyl-acetonitrile with the ethyl ester of a 4-substituted phenylacetic acid. The table summarizes the results reported by the submitters. 

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