HCID 58524150, compound → HCID 18365523, compound

HRID 536432Notes

Reaction equation

HRID 536432 reaction equation
[CH3:1][C:2]1[C:3]([N+:13]([O-])=O)=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6]>CO.[Pd]>[CH3:1][C:2]1[C:3]([NH2:13])=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 1

HCID 58524150HCID 58524150, compound

Product 1

HCID 18365523HCID 18365523, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of methyl 3,4-dimethyl-2-nitrobenzoate (23 g) and Pd/C (2.3 g) in methanol (400 ml) was stirred under hydrogen (1 bar) for 48 h and filtered through Celite under nitrogen atmosphere. Evaporation of methanol gave methyl 3,4-dimethyl-2-aminobenzoate (20 g). 1H-NMR (400 MHz, CDCl3): 7.67 (d, 1H), 6.6 (d, 1H), 3.86 (s, 3H), 2.27 (s, 3H), 2.1 (s, 3H).

Workup

  1. filtrationfiltered through Celite under nitrogen atmosphere
  2. customEvaporation of methanol

Sources & evidence

ORD record
ord-eb5afdc45fd640fcb7526c99540aac1e
Source dataset
uspto-grants-2014_10
Patent number
US08859592B2

Reaction notes

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