Acetic Acid → 4'-Amino-2'-fluoro-5'-(o-methoxyanilino)acetanilide

HRID 1078012Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]([N+:12]([O-])=O)[C:9]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6].C(O)(=O)C>C(OCC)(=O)C.C(Cl)Cl.[Fe]>[NH2:12][C:10]1[C:9]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])=[CH:8][C:3]([NH:4][C:5](=[O:7])[CH3:6])=[C:2]([F:1])[CH:11]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 2'-fluoro-5'-(o-methoxyanilino)-4'-nitroacetanilide (14.6 g, 0.046 mol) in ethyl acetate is slowly added to a mixture of iron powder (7.65 g, 0.137 mol) in a 5% acetic acid solution at 65° C. After the addition is complete, the reaction mixture is heated at 65° C. overnight, treated with additional iron powder (2.55 g), heated at 65° C. for one hour and filtered. The resultant filtrate is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a brown oil. Flash column chromatography of the oil using silica gel and 10% to 30% ethyl acetate in methylene chloride solutions gives the title product as a brown oil which is identified by NMR spectral analyses.

Workup

additionAfter the addition
temperatureheated at 65° C. for one hour
filtrationfiltered
extractionThe resultant filtrate is extracted with ethyl acetate
washwashed sequentially with water and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customto obtain a brown oil

Sources & evidence

ORD record: ord-b516a13421474b5cb1c3b6bcf9845312
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05545742

Reaction notes

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