Citric Acid → 5-fluoro-1,3-dihydro-2H-indol-2-one

HRID 2360078Notes

Reaction equation

HRID 2360078 reaction equation
[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:12]([CH3:29])=[C:13](/[CH:17]=[C:18]2/[C:19]3[CH:20]=[C:21]([F:28])[CH:22]=[CH:23][C:24]=3[NH:25][C:26]/2=[O:27])[NH:14][C:15]=1[CH3:16])=[O:10])[CH2:4][CH3:5].[C:30]([OH:42])(=[O:41])[CH2:31][C:32]([CH2:37][C:38]([OH:40])=[O:39])([C:34]([OH:36])=[O:35])[OH:33]>C(O)C>[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:12]([CH3:29])=[C:13](/[CH:17]=[C:18]2/[C:19]3[CH:20]=[C:21]([F:28])[CH:22]=[CH:23][C:24]=3[NH:25][C:26]/2=[O:27])[NH:14][C:15]=1[CH3:16])=[O:10])[CH2:4][CH3:5].[C:30]([O-:42])(=[O:41])[CH2:31][C:32]([CH2:37][C:38]([O-:40])=[O:39])([C:34]([O-:36])=[O:35])[OH:33].[F:28][C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][CH:22]=1)[NH:25][C:26](=[O:27])[CH2:18]2

Participants

5

Reactant 2

HCID 311Citric AcidHCID 5329102Sunitinib

Product 2

HCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 86658825HCID 86658825, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sunitinib (1.19 g, 2.99 mmol) dissolved in ethanol (120 ml) and citric acid (0.63 g, 3.29 mmol) dissolved in ethanol (10 ml) were combined while heating, and left to cool to room temperature to give sunitinib citrate with melting points 167-173° C. (Form I), 185-198° C. (Form II) and 215-222° C. (Form III).

Workup

  1. temperaturewhile heating
  2. waitleft

Sources & evidence

ORD record
ord-d7cc5c5ce27a44d2887bfa086267858f
Source dataset
uspto-grants-2014_04
Patent number
US08686023B2

Reaction notes

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