Methyl 2-methyl-5-nitrobenzoate → Methyl 5-Amino-2-methylbenzoate

HRID 1960110Notes

Reaction equation

HRID 1960110 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>CO.[Pd]>[NH2:12][C:9]1[CH:10]=[CH:11][C:2]([CH3:1])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 4377758Methyl 2-methyl-5-nitrobenzoate

Product 1

HCID 15049977Methyl 5-Amino-2-methylbenzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-methyl-5-nitrobenzoate (60 g, 307 mmol) in MeOH (600 mL) was added Pd (10 wt % on carbon) (1.6 g). The reaction was shaken under hydrogen (30-50 psi) for 1 h, filtered through a celite pad and concentrated to afford the desired product as a red paste, which was used in the next step without purification.

Workup

  1. filtrationfiltered through a celite pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4aeb9cf4a3f240afa5a5af979f67f1d2
Source dataset
uspto-grants-2013_04
Patent number
US08410284B2

Reaction notes

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