Nitric Acid → 2-(3-Amino-4-hydroxyphenyl)propanenitrile
Reaction equation
OC1C=CC(C(C)C#N)=CC=1.[N+]([O-])(O)=O.[N+:16]([C:19]1[CH:20]=[C:21]([CH:26]([CH3:29])[C:27]#[N:28])[CH:22]=[CH:23][C:24]=1[OH:25])([O-])=O.[H][H]>C(O)(=O)C.C(O)C.[Pd]>[NH2:16][C:19]1[CH:20]=[C:21]([CH:26]([CH3:29])[C:27]#[N:28])[CH:22]=[CH:23][C:24]=1[OH:25]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
4-Hydroxy-phenyl-propionitrile is nitrated in glacial acetic acid with 65% strength nitric acid at 10°-15° C, in the course of 2 hours, the 3-nitro-4-hydroxyphenyl-propionitrile (melting point = 104° C) is reduced with hydrogen, using 5% strength palladium charcoal as the catalyst, in ethanol at room temperature to give 3-amino-4-hydroxyphenyl-propionitrile (melting point = 125° C) and the amine compound is acetylated in toluene with molar equivalent amounts of acetic anhydride. The 3-acetamino-4-hydroxyphenyl-propionitrile (melting point = 191°-192°) is slowly warmed to 250°-260° and then rapidly heated up to 300°. The melt is cooled to room temperature, the oil is taken up in an alkaline aqueous solution, the pH of which is adjusted to 10, and the water/oil emulsion is extracted by shaking with chloroform. The chloroform solution is separated from the aqueous phase, dried with sodium sulphate and concentrated. The pink-beige needle crystals thus obtained melt at 69°-70° C.
Sources & evidence
- ORD record
- ord-b60f5900053a429ab0d703138520668a
- Source dataset
- uspto-grants-1978_01
- Patent number
- US04066830
Reaction notes
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