Acetic Acid → N-(2-Amino-4-bromophenyl)-2-chloroacetamide

HRID 44186Notes

Reaction equation

[Cl-].[NH4+].C(O)(=O)C.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:18])[CH2:16][Cl:17])=[C:10]([N+:19]([O-])=O)[CH:9]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.CN(C=O)C>[NH2:19][C:10]1[CH:9]=[C:8]([Br:7])[CH:13]=[CH:12][C:11]=1[NH:14][C:15](=[O:18])[CH2:16][Cl:17]

Participants

Conditions

Temperature: 50 °C

Procedure

Ferrous powder (19.8 g, 354 mmol), ammonium chloride (1.1 g, 19.7 mmol) and acetic acid (4.9 ml, 86.5 mmol) were suspended in 300 ml water and stirred at 50° C. for 15 min. To this mixture, a solution of N-(4-bromo-2-nitrophenyl)-2-chloroacetamide (11.5 g, 39.3 mmol) in 100 ml DMF was added quickly. After stirring for 15 min, the mixture was basified to pH 9 with aqueous sodium carbonate solution. The remaining solids were filtered and washed with water and ethyl acetate. Extraction of the water layer with ethyl acetate, washing of the combined organic layers with brine, drying over MgSO4, removing the solvent under reduced pressure and purification of the crude product by flash chromatography on silica gel (petroleum ether/ethyl acetate, 1/1) yielded N-(2-amino-4-bromophenyl)-2-chloroacetamide (4.5 g, 17.0 mmol, 43%) as an off-white solid.

Workup

stirringAfter stirring for 15 min
filtrationThe remaining solids were filtered
washwashed with water and ethyl acetate
extractionExtraction of the water layer with ethyl acetate
washwashing of the combined organic layers with brine
dry with materialdrying over MgSO4
customremoving the solvent
customunder reduced pressure and purification of the crude product by flash chromatography on silica gel (petroleum ether/ethyl acetate, 1/1)

Sources & evidence

ORD record: ord-43f833b971914c87909b782e12612778
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541404B2

Reaction notes

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