4-Fluorobenzoic Acid → Methyl 2-(4-fluoro-benzoylamino)-3-hydroxy-benzoate

HRID 401637Notes

Reaction equation

HRID 401637 reaction equation
[NH2:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O>[F:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:1][C:2]2[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[O:19])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 99734-Fluorobenzoic AcidHCID 205248Anthranilic acid, 3-hydroxy-, methyl esterHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 59625786Methyl 2-(4-fluoro-benzoylamino)-3-hydroxy-benzoateYield 84.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.0 g (4.9 mmol) of methyl 2-amino-3-hydroxybenzoate 9bb, 1.03 g (7.4 mmol) of 4-fluorobenzoic acid 9 cc, 10 mL DMF and 2.9 mL (20.6 mmol) of TEA were placed into a flask and stirred for 10 min. HATU (7.4 mmol, 2.8 g) was added and the reaction was stirred overnight. The reaction mixture was poured into water and extracted with EtOAc. The organics were washed with water and brine and the solvent was evaporated to give 1.2 g of crude product, methyl 2-(4-fluoro-benzoylamino)-3-hydroxy-benzoate, 9dd, which was used without purification. MS m/z (M+H+) 290.1.

Workup

  1. stirringthe reaction was stirred overnight
  2. extractionextracted with EtOAc
  3. washThe organics were washed with water and brine
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b09bd68f31074e75906006922ccdaf85
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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