Methanol → Methyl 3-amino-4-propylbenzoate

HRID 1699899Notes

Reaction equation

HRID 1699899 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][CH3:15])[C:7]([OH:9])=[O:8])([O-])=O.S(=O)(=O)(O)O.[CH3:21]O>[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH2:13][CH2:14][CH3:15])[C:7]([O:9][CH3:21])=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 155216373-Nitro-4-propylbenzoic acid

Product 1

HCID 22387873Methyl 3-amino-4-propylbenzoate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To 3-nitro-4-propylbenzoic acid (31.0 g) were added sulfuric acid (1.0 g) and methanol (300 ml) and the mixture was heated under reflux for 24 hr. After cooling, 5% Pd-C (0.60 g) was added to the reaction mixture and the mixture was stirred under a hydrogen atmosphere (normal pressure) for 6 hr. The reaction mixture was filtered through Celite and concentrated. To the residue was added a saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with toluene. The toluene layer was dried over sodium sulfate and concentrated to give the object compound (28.7 g) as an brown oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hr
  3. temperatureAfter cooling
  4. filtrationThe reaction mixture was filtered through Celite
  5. concentrationconcentrated
  6. additionTo the residue was added a saturated aqueous sodium hydrogencarbonate solution
  7. extractionthe mixture was extracted with toluene
  8. dry with materialThe toluene layer was dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5dab9245f11e442489c39e4490cdb2a3
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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