Methyl 3-methoxy-4-nitrobenzoate → Methyl 4-amino-3-methoxybenzoate

HRID 1436078Notes

Reaction equation

HRID 1436078 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].[H][H]>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 287308Methyl 3-methoxy-4-nitrobenzoateHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% palladium-carbon (containing 50% water, 15 g) was added to a solution of methyl 3-methoxy-4-nitrobenzoate (150 g) in methanol (600 mL) and THF (300 mL), and the reaction solution was stirred at a hydrogen pressure of 0.9 MPa at 50° C. to 64° C. for 6.5 hours. The reaction solution was left to cool to room temperature and then filtered through celite. The resulting filtrate was concentrated under reduced pressure to obtain 134 g of the title compound. The property values corresponded to the reported values (CAS #41608-64-4).

Workup

  1. waitThe reaction solution was left
  2. filtrationfiltered through celite
  3. concentrationThe resulting filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0327eb3acc264ed598439299d30b43cc
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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