Ammonium formate → N-(5-acetyl-2-hydroxyphenyl)methanesulfonamide

HRID 2357038Notes

Reaction equation

HRID 2357038 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([O:15]CC2C=CC=CC=2)=[C:8]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH:9]=1)(=[O:3])[CH3:2].C([O-])=O.[NH4+]>CO>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:15])=[C:8]([NH:10][S:11]([CH3:14])(=[O:12])=[O:13])[CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 123639231-(4-Benzyloxy-3-methanesulphonamidophenyl)ethanone

Product 1

HCID 19073226N-(5-acetyl-2-hydroxyphenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In an atmosphere of nitrogen 10% Pd—C (1.17 g) was added to a mixture of compound of example 39c (11.7 g; 36.67 mmol) and ammonium formate (11.56 g; 116.23 mmol) in methanol (110 mL) It was refluxed for 3 h. The catalyst was filtered and the filtrate concentrated and purified using flash chromatography (silica gel, 10% CH3CN in chloroform). Yield, 8.3 g (84.2%); mp, 202° C.: MS (ESI−): 228 (M−1); analysis: C9H11NO4S requires C, 47.15; H, 4.84; N, 6.11; S, 13.98; found: C, 47.39; H, 4.72; N, 6.53; S, 13.53%.

Workup

  1. temperaturewas refluxed for 3 h
  2. filtrationThe catalyst was filtered
  3. concentrationthe filtrate concentrated
  4. custompurified
  5. customYield
  6. custommp, 202° C.

Sources & evidence

ORD record
ord-bf88218d073d4e059a8970f7d2c337be
Source dataset
uspto-grants-2010_07
Patent number
US07759387B2

Reaction notes

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