Water → Methyl 2-amino-4-fluorobenzoate

HRID 1924413Notes

Reaction equation

HRID 1924413 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][Si](C=[N+]=[N-])(C)C.O>CO.C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 167693TrimethylsilyldiazomethaneHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 14075433Methyl 2-amino-4-fluorobenzoateYield 95.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

2-Amino-4-fluorobenzoic acid (10.0 g, 64.5 mmol) was dissolved in methanol (50 mL) and toluene (150 mL). (Trimethylsilyl)diazomethane (2M in diethyl ether, 48.3 mL, 96.7 mmol) was added over 10 minutes at RT. Stirring was continued for 2 h at RT. Water (300 mL) was added to the mixture and the volatiles were removed in vacuo. The remaining aqueous phase was cooled to 0° C. for 30 minutes and the formed precipitate was collected by filtration, washed with water and dried to give pure title compound (10.4 g, 95%).

Workup

  1. customthe volatiles were removed in vacuo
  2. filtrationthe formed precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-80c573e0d42946fba48078105dd6de80
Source dataset
uspto-grants-2012_05
Patent number
US08178544B2

Reaction notes

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