Ethyl Acetate → Methyl 3-amino-4-methylbenzoate

HRID 1987318Notes

Reaction equation

HRID 1987318 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([N+:11]([O-])=O)[CH:5]=1.CCOC(C)=O>CO.[Pd]>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([NH2:11])[CH:5]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 81816Methyl 4-methyl-3-nitrobenzoate

Product 1

HCID 337778Methyl 3-amino-4-methylbenzoateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The ester from above (29.37 g, 150 mmol) was added to a 2 L Parr hydrogenation flask and dissolved in anhydrous MeOH (200 mL) plus EtOAc (25 mL). The solution was then treated with 10% Pd/C (2.25 g, 50% wet) and fitted to a hydrogenator apparatus. After purging the flask 3 times with hydrogen gas, the mixture was shaken for 1 hour at 30 psi. The flask was then removed, and filtered through a celite pad washing with MeOH. The solvent was then removed under reduced pressure to afford 3-amino-4-methyl-benzoic acid methyl ester as a white solid (25.0 g, 100%). 1H NMR(CDCl3) δ 2.21 (s, 3H), 3.70 (br s, 2H, NH2), 3.88 (s, 3H), 7.10 (d, 1H, J=7.5 Hz), 7.35 (s, 1H), 7.37 (d, 1H, J=8.4 Hz).

Workup

  1. customfitted to a hydrogenator apparatus
  2. customAfter purging the flask 3 times with hydrogen gas
  3. customThe flask was then removed
  4. filtrationfiltered through a celite pad
  5. washwashing with MeOH
  6. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-ac9428abe86c401189e8736862adf29d
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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