2-Methoxy-6-nitrobenzonitrile → 2-Amino-6-hydroxybenzonitrile

HRID 471615Notes

Reaction equation

HRID 471615 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

HCID 380482-Methoxy-6-nitrobenzonitrile

Product 1

HCID 542287732-Amino-6-hydroxybenzonitrileYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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

  1. filtrationthe mixture was filtered
  2. washthe catalyst was washed with EtOAc (150 mL)
  3. extractionThe combined extract
  4. customwas evaporated

Sources & evidence

ORD record
ord-14ea514a80944885bb60223b27c536ea
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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