Ethyl Acetate → Methyl 2-amino-3-methoxybenzoate

HRID 2206699

Reaction equation

HRID 2206699 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:13]([O-])=O)=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].CCOC(C)=O>C1COCC1.CO.[Pd]>[NH2:13][C:4]1[C:3]([O:2][CH3:1])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 79195Benzoic acid, 3-methoxy-2-nitro-, methyl ester

Product 1

HCID 602320Methyl 2-amino-3-methoxybenzoateYield 99.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of compound 52 (26.2 g, 124 mmol) and Pd/C (10 wt. %, 6.0 g) in THF (400 mL) and MeOH (200 mL) was stirred under an atmosphere of H2 at room temperature for 18 hours. EtOAc (300 mL) was added to the mixture and filtered through a Celite pad. The filtrate was concentrated in vacuo to provide the crude product 53 (22.4 g, 99%) as colorless oil.

Workup

  1. filtrationfiltered through a Celite pad
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f29ead4b9b4b443baed769dc2288e81c
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Linked notes

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