Ethyl Acetate → Methyl 2-amino-3-methoxybenzoate

HRID 576326Notes

Reaction equation

HRID 576326 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-08f1985b2e514371aac935c3e9cd63df
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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