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

HRID 2114874
Notes
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Reaction equation

HRID 2114874 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]([NH2:19])([CH3:18])[CH3:17].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]([CH:16]([CH3:18])[CH3:17])[C:13](=[O:15])[CH2:12]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6363IsopropylamineHCID 11951676(2,3-Difluoro-5-nitrophenyl)acetic acid

Product 1

HCID 119518507-Fluoro-1-isopropyl-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 (16, 1.00 g, 0.00461 mol) and isopropylamine (6 eq., 2.35 ml, 0.0276 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 resulting precipitate is filtered, washed with water and ether, and dried under vacuum (0.39 g, 35%); HPLC r.t. 5.31 min.

Workup

  1. stirringthe mixture stirred at room temperature for 1 hour
  2. filtrationThe resulting precipitate is filtered
  3. washwashed with water and ether
  4. customdried under vacuum (0.39 g, 35%)

Sources & evidence

ORD record
ord-3ee7ece6e31946d496002b2eb4f61688
Source dataset
uspto-grants-2008_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07435751B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes