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

HRID 2114891Notes

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.[CH2:16]([NH2:19])[CH2:17][CH3:18].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:19]([CH2:16][CH2:17][CH3:18])[C:13](=[O:15])[CH2:12]2

Participants

Conditions

Temperature: 50 °C

Procedure

Crude (2,3-difluoro-5-nitrophenyl) acetic acid (2.00 g, 9.2 mmol) and n-propylamine (6 eq., 4.54 ml, 0.0553 mol) are mixed in DMSO (10 ml) and stirred at 50° C. for 2 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% Ethylacetate/hexane) to give the title compound as a yellow solid. HPLC r.t. 5.40 min; MS for C11H11FN2O3 m/z 239.1 (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% Ethylacetate/hexane)

Sources & evidence

ORD record: ord-3ea1432df25e4094b7ab80847184fefb
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435751B2

Reaction notes

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