Methyl[(2-hydroxy-3-nitrobenzoyl)methylamino]acetate → Methyl[(3-amino-2-hydroxybenzoyl)methylamino]acetate

HRID 1528212Notes

Reaction equation

HRID 1528212 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][NH:5][CH2:6][C:7](=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[C:9]=1[OH:17].[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:19])[CH2:4][NH:5][CH2:6][C:7](=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[C:9]=1[OH:17]

Participants

5

Reactant 2

HCID 131733217Methyl[(2-hydroxy-3-nitrobenzoyl)methylamino]acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 131733216Methyl[(3-amino-2-hydroxybenzoyl)methylamino]acetateYield 76.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5.78 g (21.5 mmol, 1 eq) of methyl[(2-hydroxy-3-nitrobenzoyl)methylamino]acetate in 75 ml of methanol in the presence of 0.52 g (10% by weight) of Pd/C 10% was stirred at hydrogen atmospheric pressure for two and a half hours. The reaction medium was filtered through celite and the filtrate was evaporated. The residue (4.78 g) was chromatographed on silica gel (300 g prepacked column, eluent heptane/ethyl acetate from 40% to 90% of ethyl acetate, 120 ml/min). 3.92 g of methyl[(3-amino-2-hydroxybenzoyl)methylamino]acetate were obtained in the form of a yellow oil. Yield=76%.

Workup

  1. filtrationThe reaction medium was filtered through celite
  2. customthe filtrate was evaporated
  3. customThe residue (4.78 g) was chromatographed on silica gel (300 g prepacked column, eluent heptane/ethyl acetate from 40% to 90% of ethyl acetate, 120 ml/min)

Sources & evidence

ORD record
ord-9c9e5fd81b0f46d381ef7e9c768be811
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

Loading…