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

HRID 1852592Notes

Reaction equation

HRID 1852592 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-dcb0930d944947908c5cd45810bf4af8
Source dataset
uspto-grants-2015_02
Patent number
US08962607B2

Reaction notes

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