3-Acetylamino-6-bromo-2-nitro-benzoic acid → Methyl 3-acetylamino-6-bromo-2-nitrobenzoate

HRID 887747

Reaction equation

HRID 887747 reaction equation
[C:1]([NH:4][C:5]1[C:6]([N+:15]([O-:17])=[O:16])=[C:7]([C:11]([Br:14])=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:3])[CH3:2].[CH3:18][Si](C=[N+]=[N-])(C)C.C(OCC)C>CO.O1CCCC1>[C:1]([NH:4][C:5]1[C:6]([N+:15]([O-:17])=[O:16])=[C:7]([C:11]([Br:14])=[CH:12][CH:13]=1)[C:8]([O:10][CH3:18])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 114039033-Acetylamino-6-bromo-2-nitro-benzoic acidHCID 23159941trimethylsilyldiazomethane Et2O

Product 1

HCID 11151255Methyl 3-acetylamino-6-bromo-2-nitrobenzoateYield 66.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 3-(acetylamino)-6-bromo-2-nitrobenzoic acid (2.00 g, 6.60 mmol) in methanol (20 mL) and tetrahydrofuran (5 mL) was added 2M trimethylsilyldiazomethane/diethyl ether solution (10.6 mL, 21.1 mmol) under ice-cooling, and the mixture was stirred at room temperature for 5 days. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→60/40) to give the title compound (1.39 g, yield 66%).

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→60/40)

Sources & evidence

ORD record
ord-ab75b8843663424d92e2efdb870c0921
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Linked notes

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