Diethyl Ether → Methyl 6-amino-2,3,4-trimethoxybenzoate

HRID 536067Notes

Reaction equation

HRID 536067 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:11][CH3:12])[C:5]([O:13][CH3:14])=[C:4]([O:15][CH3:16])[CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:18].CCOCC>C1COCC1.CO>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:18])=[O:9])=[C:6]([O:11][CH3:12])[C:5]([O:13][CH3:14])=[C:4]([O:15][CH3:16])[CH:3]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 130363926-Amino-2,3,4-trimethoxybenzoic acid

Product 1

HCID 606724Methyl 6-amino-2,3,4-trimethoxybenzoateYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-amino-2,3,4-tris(methyloxy)benzoic acid (2.7 g, 11.88 mmol) in THF (20 mL) and MeOH (20 mL) at 25° C. was treated with a solution of 2M TMS-diazomethane in Et2O (14.85 mL, 29.7 mmol) and stirred for 10 minutes before being concentrated to give methyl 6-amino-2,3,4-tris(methyloxy)benzoate (2.87 g, 99%) as a brown solid. MS (m/z) 242.1 (M+H+).

Workup

  1. concentrationbefore being concentrated

Sources & evidence

ORD record
ord-0ea60f2d625c4af5a23ce63fd8defe54
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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