4-Amino-5-chloro-2-methoxybenzoic acid → Methyl 4-amino-5-chloro-2-methoxybenzoate

HRID 2113368Notes

Reaction equation

HRID 2113368 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[CH3:14][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO>[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][C:5]([C:6]([O:8][CH3:14])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

5

Reactant 2

HCID 816264-Amino-5-chloro-2-methoxybenzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 700493Methyl 4-amino-5-chloro-2-methoxybenzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 4-amino-5-chloro-2-methoxybenzoic acid (1.008 g, 5.0 mmol) in a mixture of toluene (9 mL) and methanol (1 mL) at 0° C. was added (trimethylsilyl)diazomethane (2.0 M in hexane, 3.0 mL, 6.0 mmol) dropwise. The reaction mixture was then warmed to room temperature and stirred for 16 h. Excess (trimethylsilyl)diazomethane was quenched by adding acetic acid until the bright yellow color of the reaction mixture disappeared. The mixture was then concentrated in vacuo to give the title compound as an off-white solid, which was used without further purification.

Workup

  1. customExcess (trimethylsilyl)diazomethane was quenched
  2. additionby adding acetic acid until the bright yellow color of the reaction mixture
  3. concentrationThe mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-80c4199b2e5d402cbc5895da10d255b2
Source dataset
uspto-grants-2009_04
Patent number
US07524959B2

Reaction notes

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