Trimethylsilyldiazomethane → Methyl 2-amino-4-fluorobenzoate

HRID 884450

Reaction equation

HRID 884450 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH2:11])[CH:3]=1.[CH3:12][Si](C=[N+]=[N-])(C)C>O1CCCC1.CO>[CH3:12][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[NH2:11]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 14075433Methyl 2-amino-4-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 4-fluoro-2-aminobenzoic acid (2.68 g; 17.3 mmol) in dry tetrahydrofuran (60 mL) and MeOH (10 mL) was added a solution of trimethylsilyldiazomethane in hexanes (12 mL of 2.0 N; 24 mmol) via syringe over 20 minutes under nitrogen atmosphere. The resulting solution was allowed to warm to room temperature and stirred for 2 hours then concentrated in vacuo to provide the ester a light yellow solid (˜100%).

Workup

  1. temperatureto warm to room temperature
  2. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-169bf3f1be0344998676ed606756c57c
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Linked notes

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