2-Methoxy-6-nitrobenzonitrile → 2-Amino-6-hydroxybenzonitrile
Reaction equation
C[O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[C:4]=1[C:5]#[N:6]>CCO.[Pd]>[NH2:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:3]([OH:2])[C:4]=1[C:5]#[N:6]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 2-methoxy-6-nitrobenzonitrile (Example 1290 (1.11 g, 6.76 mmol) in EtOH (120 mL) was hydrogenated over a catalytic amount of 10% Pd/C (0.15 g) at room temperature under hydrogen (1 atm). After 2 h, the mixture was filtered and the catalyst was washed with EtOAc (150 mL). The combined extract was evaporated, to give 1.11 g (100%) of the title compound as a brown solid. The crude product was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ 10.39 (broad s, 1H), 7.00 (t, J=8.0 Hz, 1H), 6.12-6.17 (m, 1H), 6.01-6.05 (m, 1H), 5.77 (broad s, 2H).
Workup
- filtrationthe mixture was filtered
- washthe catalyst was washed with EtOAc (150 mL)
- extractionThe combined extract
- customwas evaporated
Sources & evidence
- ORD record
- ord-14ea514a80944885bb60223b27c536ea
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633186B2
Reaction notes
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