Hydrochloric Acid → 1-Cyclopropyl-7-fluoro-5-nitro-1,3-dihydro-indol-2-one

HRID 2114897Notes

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.[CH:16]1([NH2:19])[CH2:18][CH2:17]1.Cl>CS(C)=O>[CH:16]1([N:19]2[C:2]3[C:3](=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[CH:6][C:7]=3[F:8])[CH2:12][C:13]2=[O:15])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 50 °C

Procedure

Crude (2,3-difluoro-5-nitrophenyl) acetic acid (2.50 g, 11.5 mmol) and cyclopropylamine (6 eq., 4.78 ml, 0.0691 mol) are mixed in DMSO (10 ml) and stirred at 50 ° C. for 20 hours. 2N Hydrochloric acid (40 ml) is added in one portion and the mixture stirred at room temperature for 2 hours. The resulting light yellow precipitate is filtered, washed with water and dried under vacuum. The residue is purified by flash column chromatography (20% Ethyl acetate/hexane) to give the title compound as a yellow solid. HPLC r.t. 4.90 min; MS for C11H9FN2O3 m/z 235.0 (M−H)−.

Workup

stirringthe mixture stirred at room temperature for 2 hours
filtrationThe resulting light yellow precipitate is filtered
washwashed with water
customdried under vacuum
customThe residue is purified by flash column chromatography (20% Ethyl acetate/hexane)

Sources & evidence

ORD record: ord-13e0ca1ba8bb443095a76e34f529e8d0
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435751B2

Reaction notes

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