Water → 2-(4-Fluorobenzoylamino)-4-methoxy-3-methyl-benzoic acid methyl ester

HRID 1443456Notes

Reaction equation

HRID 1443456 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH3:22])[C:15]=1[NH2:23].O>ClCCl.N1C=CC=CC=1>[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH3:22])[C:15]=1[NH:23][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 99734-Fluorobenzoic AcidHCID 59165444Methyl 2-amino-4-methoxy-3-methylbenzoate

Product 1

HCID 591654192-(4-Fluorobenzoylamino)-4-methoxy-3-methyl-benzoic acid methyl esterYield 61%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

4-Fluoro benzoic acid (700 mg, 5 mmol) was dissolved in dichloromethane (20 ml) and pyridine (2 ml). 2-Amino-4-methoxy-3-methyl-benzoic acid methyl ester (81) (878 mg, 4.5 mmol) was added and the mixture was refluxed for 5 h. Water was added and the mixture was extracted with dichloromethane. The organic phase was dried, filtered and evaporated and the afforded residue was purified by column chromatography on silica gel, eluted with ether-pentane 1:1 which gave pure title compound (870 mg, 61%). MS (M+H+) 318.

Workup

  1. temperaturethe mixture was refluxed for 5 h
  2. extractionthe mixture was extracted with dichloromethane
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customevaporated
  6. customthe afforded residue was purified by column chromatography on silica gel
  7. washeluted with ether-pentane 1:1 which

Sources & evidence

ORD record
ord-e806d96b18c04e19a87f0e973e5afb92
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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