ChemicalBook CAS DataBase List 4-AMINO-3-HYDROXY-BENZONITRILE

4-AMINO-3-HYDROXY-BENZONITRILE synthesis

5synthesis methods

Product Name:4-AMINO-3-HYDROXY-BENZONITRILE
CAS Number:55586-26-0
Molecular formula:C7H6N2O
Molecular Weight:134.14

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7772-99-8 Synthesis

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Yield: 77%

Reaction Conditions:

in acetic acid

Steps:

5 b)Preparation of 2-amino-5-cyanophenol
b)Preparation of 2-amino-5-cyanophenol A mixture of 6cyano2-nitrophenol(2.40 g, 14.6 mmol) and tin (II) chloride (9.6 g, 43.2 mmol) in acetic acid(100 mL) was heated at 80° C. under argon. After 2 hours, the starting material had disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH 7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO₄ and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH₂Cl₂) gave the desired product(1.50 g, 77%). ¹H NMR (CD₃OD): δ6.92 (d, 1H), 6.85-6.69 (m,2H).

References:

SmithKline Beecham Corporation US6271261, 2001, B1