Methyl 2-[p-(5-acetamido-4-fluoro-2-nitroanilino)phenoxy]propionate → Methyl 2-[p-(5-acetamido-2-amino-4-fluoroanilino)phenoxy]propionate

HRID 1078008Notes

Reaction equation

[C:1]([NH:4][C:5]1[C:6]([F:28])=[CH:7][C:8]([N+:25]([O-])=O)=[C:9]([CH:24]=1)[NH:10][C:11]1[CH:23]=[CH:22][C:14]([O:15][CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=1)(=[O:3])[CH3:2]>[Fe].C(O)(=O)C>[C:1]([NH:4][C:5]1[C:6]([F:28])=[CH:7][C:8]([NH2:25])=[C:9]([CH:24]=1)[NH:10][C:11]1[CH:23]=[CH:22][C:14]([O:15][CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:13][CH:12]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

Methyl 2-[p-(5-acetamido-4-fluoro-2-nitroanilino)phenoxy]propionate (8.2 g, 0.021 mol) is added to a mixture of iron dust (3.51 g, 0.063 mol) in a 5% acetic acid solution at 65° C. The reaction mixture is stirred at 65° C. for 2.5 hours, treated with additional iron dust (0.5 g), stirred at 65° C. for 30 minutes, cooled to room temperature and filtered through diatomaceous earth. The resultant filtrate is poured into water and extracted with ethyl acetate. The organic extracts are combined, washed sequentially with saturated sodium hydrogen carbonate solution and water, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title product as a brown-black solid.

Workup

stirringstirred at 65° C. for 30 minutes
temperaturecooled to room temperature
filtrationfiltered through diatomaceous earth
additionThe resultant filtrate is poured into water
extractionextracted with ethyl acetate
washwashed sequentially with saturated sodium hydrogen carbonate solution and water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-7afad48e7e524305b51ceb5521854a3c
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05545742

Reaction notes

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