Hydrochloric Acid → 7-Fluoro-1-methyl-5-nitro-1,3-dihydro-indol-2-one

HRID 2114869Notes

Reaction equation

F[C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][C:13]([OH:15])=O.[CH3:16][NH2:17].O.Cl>CS(C)=O>[F:8][C:7]1[CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=[C:3]2[C:2]=1[N:17]([CH3:16])[C:13](=[O:15])[CH2:12]2

Participants

Conditions

Temperature: 45 °C

Procedure

Crude (2,3-difluoro-5-nitrophenyl)acetic acid (12, 1.00 g, 0.00461 mol) and a 40% solution of methylamine in water (3 eq., 1.20 ml, 0.0138 mol) are mixed in DMSO (5 ml) and stirred at 45° C. for 1 hour. 2N Hydrochloric acid (20 ml) is added in one portion and the mixture stirred at room temperature for 1 hour. The reaction mixture is extracted with ethyl acetate and the extract washed with saturated aqueous sodium bicarbonate and brine, dried (MgSO4) and evaporated. The residue is purified by flash column chromatography (50% ethyl acetate/hexane) to give the title compound as a solid. HPLC r.t. 4.4 min.

Workup

stirringthe mixture stirred at room temperature for 1 hour
extractionThe reaction mixture is extracted with ethyl acetate
washthe extract washed with saturated aqueous sodium bicarbonate and brine
dry with materialdried (MgSO4)
customevaporated
customThe residue is purified by flash column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-b457b77ac1fc43cfaa66861c5d21f889
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435751B2

Reaction notes

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