3,4-Dimethoxy-6-nitrobenzamide → 2-Amino-4,5-dimethoxybenzamide

HRID 336692Notes

Reaction equation

HRID 336692 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[C:5]([N+:14]([O-])=O)[CH:4]=1>CO.[Pd]>[NH2:14][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[CH:10][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

4

Reactant 1

HCID 27361933,4-Dimethoxy-6-nitrobenzamide

Product 1

HCID 108672362-Amino-4,5-dimethoxybenzamideYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4,5-dimethoxy-2-nitrobenzamide (10 g, 44.24 mmol) in MeOH (260 mL) was mixed with palladium/carbon (2 g) and subjected to hydrogenation (50 psi) for 20 h. The reaction mixture was filtered through a Celite pad, concentrated to yield 8.7 g of 2-amino-4,5-dimethoxybenzamide (100%).

Workup

  1. filtrationThe reaction mixture was filtered through a Celite pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-cce8ff4ba9f14c3abe0363a54550c668
Source dataset
uspto-grants-2014_11
Patent number
US08889698B2

Reaction notes

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