Water → Methyl 4-amino-3-methoxybenzoate

HRID 2076264Notes

Reaction equation

HRID 2076264 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O)[C:6]([O:8][CH3:9])=[O:7].O>CO.C1COCC1.[C].[Pd]>[NH2:13][C:12]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 2

HCID 962WaterHCID 287308Methyl 3-methoxy-4-nitrobenzoate

Product 1

HCID 602411Methyl 4-amino-3-methoxybenzoateYield 104.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-methoxy-4-nitrobenzoate (150 g) in methanol (600 mL) and THF (300 mL) was added 10% palladium-carbon (a 50% water-containing product, 15 g), and the reaction liquid was stirred at 50° C. to 64° C. under a hydrogen pressure of 0.9 MPa for 6.5 hours. The reaction liquid was allowed to stand to cool to room temperature and then filtered on celite, followed by concentrating the resultant filtrate under reduced pressure to provide 134 g of the title compound. The physical property values thereof agreed with reported values (CAS#41608-64-4).

Workup

  1. additioncontaining product, 15 g), and
  2. customthe reaction liquid
  3. customThe reaction liquid
  4. filtrationfiltered on celite
  5. concentrationby concentrating the resultant filtrate under reduced pressure

Sources & evidence

ORD record
ord-0a065cec6c194157a220453b3164f06e
Source dataset
uspto-grants-2011_04
Patent number
US07923563B2

Reaction notes

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