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

HRID 1911122Notes

Reaction equation

HRID 1911122 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. additionwas added
  2. extractionextracted with EtOAc
  3. washThe organics were washed with water and brine
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-341986aa23d64e2fae8e2333a81fb569
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

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