Acetic Acid → N-[4-amino-2-fluoro-5-(2-hydroxyphenoxy)phenyl]acetamide

HRID 1280374Notes

Reaction equation

C(O)(=O)C.[F:5][C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[C:9]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[OH:22])=[CH:8][C:7]=1[NH:23][C:24](=[O:26])[CH3:25].C(OCC)(=O)C>[Fe].O>[NH2:12][C:10]1[C:9]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[OH:22])=[CH:8][C:7]([NH:23][C:24](=[O:26])[CH3:25])=[C:6]([F:5])[CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Into a mixture of 25 ml of acetic acid and 25 ml of water was added 9.5 g of an iron powder, and the mixture was heated to 80° C. Into the mixture was added dropwise a solution composed of 10.0 g of N-[2-fluoro-5-(2-hydroxyphenoxy)-4-nitrophenyl]acetamide and 100 ml of ethyl acetate. The mixture was heated for 1 hour under reflux, then, poured into water, extracted with ethyl acetate, the organic layer was washed with water, and washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated to obtain 7.42 g of N-[4-amino-2-fluoro-5-(2-hydroxyphenoxy)phenyl]acetamide.

Workup

additionInto the mixture was added dropwise a solution
temperatureThe mixture was heated for 1 hour
temperatureunder reflux
extractionextracted with ethyl acetate
washthe organic layer was washed with water
washwashed with saturated aqueous sodium bicarbonate
dry with materialdried over magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-56bbd5674eec44f58e9a58cded7465e8
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06451740B2

Reaction notes

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