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

HRID 2120494Notes

Reaction equation

HRID 2120494 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:8]=[C:3]([C:2]([CH3:1])=[CH:11][CH:10]=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-methylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.3 g (32 mmol) of methyl 2-methyl-5-nitrobenzoate are dissolved in 80 ml of anhydrous methanol and then transferred into a steel reactor. The mixture is degassed with nitrogen and then 630 mg of Pd/C (5%) are added. The reaction medium is then subjected to a hydrogen pressure of 4 bar and to a temperature of 80° C. for 14 hours and then brought to ambient pressure and temperature and filtered. The residue, after evaporation, is purified by chromatography on a silica column. A brown oil is obtained (m=4.6 g, Y=86%).

Workup

  1. customtransferred into a steel reactor
  2. customThe mixture is degassed with nitrogen
  3. addition630 mg of Pd/C (5%) are added
  4. filtrationfiltered
  5. customThe residue, after evaporation
  6. customis purified by chromatography on a silica column
  7. customA brown oil is obtained (m=4.6 g, Y=86%)

Sources & evidence

ORD record
ord-1b38d5f2a88f4a0d90ebe0cf22cc51ef
Source dataset
uspto-grants-2004_02
Patent number
US06689922B1

Reaction notes

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