Ethanol → 4-[(5-Fluoro-2-methylbenzoyl)amino]benzoic acid

HRID 3570Notes

Reaction equation

HRID 3570 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:22])=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][CH:11]=1)=[O:8].[OH-].[Na+].O.C(O)C>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:22])=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:19][CH:20]=1)=[O:8]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 21837152Ethyl 4-[(5-fluoro-2-methylbenzoyl)amino]benzoate

Product 1

HCID 218370704-[(5-Fluoro-2-methylbenzoyl)amino]benzoic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.60 g of ethyl 4-[(5-fluoro-2-methylbenzoyl)amino]benzoate 0.60 ml of 10N NaOH, 25 ml of water and 50 ml of absolute ethyl alcohol is heated on a steam bath for 1 hour, cooled and acidified with acetic acid. The resulting solid is filtered and dried in vacuo at 60°-80° C. to give 0.47 g of the desired product as a solid, m.p. 272°-275° C.

Workup

  1. temperatureis heated on a steam bath for 1 hour
  2. temperaturecooled
  3. filtrationThe resulting solid is filtered
  4. customdried in vacuo at 60°-80° C.

Sources & evidence

ORD record
ord-25c8ef28b32b437fb9da1f69778e6b37
Source dataset
uspto-grants-1998_03
Patent number
US05733905

Reaction notes

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