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

HRID 423217Notes

Reaction equation

HRID 423217 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-9456091775ba44c8bed1ceebb8f05feb
Source dataset
uspto-grants-2012_01
Patent number
US08101766B2

Reaction notes

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