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

HRID 2114902Notes

Reaction equation

HRID 2114902 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.[NH2:16][CH2:17][CH:18]1[CH2:20][CH2:19]1.Cl>CS(C)=O>[CH:18]1([CH2:17][N:16]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])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 75646CyclopropanemethanamineHCID 11951676(2,3-Difluoro-5-nitrophenyl)acetic acid

Product 1

HCID 692741651-Cyclopropylmethyl-7-fluoro-5-nitro-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
45 °C

Procedure

Crude (2,3-difluoro-5-nitrophenyl) acetic acid (2.50 g, 11.5 mmol) and (aminomethyl)cyclopropane (6 eq., 5.98 ml, 0.0691 mol) are mixed in DMSO (10 ml) and stirred at 45° 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 ether, and dried under vacuum to give the title compound as a yellow solid. HPLC r.t. 4.91 min; MS for C12H11FN2O3 m/z 251.2 (M+H)+.

Workup

  1. stirringthe mixture stirred at room temperature for 2 hours
  2. filtrationThe resulting light yellow precipitate is filtered
  3. washwashed with water and ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8512173cf00042b1a1a8e7b8bb74eaef
Source dataset
uspto-grants-2008_10
Patent number
US07435751B2

Reaction notes

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