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

HRID 1919664Notes

Reaction equation

HRID 1919664 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>[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

3

Reactant 1

HCID 4377758Methyl 2-methyl-5-nitrobenzoate

Product 1

HCID 15049977Methyl 5-Amino-2-methylbenzoateYield 97.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-methyl-5-nitrobenzoate (5.06 g) was suspended in methanol (100 ml). The mixture was degassed by bubbling nitrogen for 15 minutes. Pd/C 10% wet Degussa type E101 NE/WW (260 mg) was added and the mixture stirred under hydrogen atmosphere (balloon) overnight. The suspension was filtered and the solvents evaporated to afford methyl 5-amino-2-methylbenzoate as an orange oil (4.18 g, 97% yield).

Workup

  1. customThe mixture was degassed
  2. customby bubbling nitrogen for 15 minutes
  3. additionPd/C 10% wet Degussa type E101 NE/WW (260 mg) was added
  4. filtrationThe suspension was filtered
  5. customthe solvents evaporated

Sources & evidence

ORD record
ord-bb4734d460ff42438500921a67b19dc9
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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