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

HRID 409894Notes

Reaction equation

HRID 409894 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=O)C.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

6

Reactant 4

HCID 6228DimethylformamideHCID 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 9a, 1.03 g (7.4 mmol) of 4-fluorobenzoic acid 9b, 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, 9c, 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-6351ae3307af43da9a7acd707f43a9b9
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

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