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

HRID 2109688Notes

Reaction equation

HRID 2109688 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.[C:14]1(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

4

Reactant 2

HCID 1140TolueneHCID 816264-Amino-5-chloro-2-methoxybenzoic acid

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-eed4716dd4514ad8a35bee75eb362c5a
Source dataset
uspto-grants-2009_04
Patent number
US07514558B2

Reaction notes

Loading…