4-Hydroxy-3-nitrobenzonitrile → 3-Amino-4-hydroxybenzonitrile
Reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[OH:12])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[OH:12]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 2-nitro-4-cyanophenol(10 g, 61 mmol) in methanol(250 mL) was added 10% Pd/C (1g). The mixture was flushed with argon, then hydrogen was bubbled through the solution for 10 min. and a hydrogen atmosphere was maintained at balloon pressure overnight. The mixture was filtered through celite and the celite was washed with methanol. The solvent was evaporated and chromatography of the resulting solid on silica gel (5% MeOH/CH2Cl2) gave the desired product(8.0 g, 97%). 1H NMR (CD3OD): d 6.96 (d, 1H), 6.90 (dd, 1H), 6.77 (d, 1H).
Workup
- customThe mixture was flushed with argon
- customhydrogen was bubbled through the solution for 10 min.
- temperaturea hydrogen atmosphere was maintained at balloon pressure overnight
- filtrationThe mixture was filtered through celite
- washthe celite was washed with methanol
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-02466f1ca124402f8570ce52cc613c1e
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06211373B1
Reaction notes
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