Toluene → Methyl 4-amino-5-chloro-2-methoxybenzoate

HRID 871221Notes

Reaction equation

HRID 871221 reaction equation
N[C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:8]=[C:9]([Cl:11])C=1)[C:5]([OH:7])=[O:6].C[Si]([CH:18]=[N+:19]=[N-])(C)C.[C:21]1(C)C=CC=CC=1>CO>[NH2:19][C:18]1[C:9]([Cl:11])=[CH:8][C:4]([C:5]([O:7][CH3:21])=[O:6])=[C:3]([O:12][CH3:13])[CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 167693TrimethylsilyldiazomethaneHCID 10750603HCID 10750603, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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-06caa0a736ad4d6d9a2fcde31a359a62
Source dataset
uspto-grants-2015_03
Patent number
US08969571B2

Reaction notes

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