Acetic Anhydride → N-(5-Acetyl-2-hydroxyphenyl)ethanimidic acid

HRID 2425017Notes

Reaction equation

HRID 2425017 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[N+:11]([O-])=O.[C:14](OC(=O)C)(=[O:16])[CH3:15]>CO.CN(C=O)C.[Pd]>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([NH:11][C:14](=[O:16])[CH3:15])[CH:4]=1)(=[O:10])[CH3:9]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 1387234-Hydroxy-3-Nitroacetophenone

Product 1

HCID 283886N-(5-Acetyl-2-hydroxyphenyl)ethanimidic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(4-hydroxy-3-nitro-phenyl)-ethanone (10 g) in methanol, DMF (50 ml) and acetic anhydride (10 ml) was hydrogenated using 10% Pd—C (0.45 g) for 2 h at 30 psi. The catalyst was filtered off. The filtrate was concentrated (5 ml) and treated with EtOAc (100 ml) to obtain the title compound, which was filtered, washed with EtOAc (10 ml) and dried. Yield, 9.1 g (85%); mp, >215° C.; MS (EI): 193 (M+), 151, 136, 108.

Workup

  1. customfor 2 h
  2. filtrationThe catalyst was filtered off
  3. concentrationThe filtrate was concentrated (5 ml)
  4. additiontreated with EtOAc (100 ml)

Sources & evidence

ORD record
ord-b5c8308542944902a7c838c91912253e
Source dataset
uspto-grants-2011_06
Patent number
US07964628B2

Reaction notes

Loading…