Dichloromethane → HCID 178485780, compound

HRID 24853Notes

Reaction equation

HRID 24853 reaction equation
C1(=O)[N:5]([CH2:6][C:7]([N:9]([C:11]2[CH:16]=[CH:15][C:14]([NH:17]/[C:18](=[C:25]3\[C:26](=[O:37])[NH:27][C:28]4[C:33]\3=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=4)/[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[CH3:10])=[O:8])C(=O)C2=CC=CC=C12.ClCCl.O.NN>C(O)C>[NH2:5][CH2:6][C:7]([N:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:17]/[C:18](=[C:25]2\[C:26](=[O:37])[NH:27][C:28]3[C:33]\2=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=3)/[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:13][CH:12]=1)[CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 178485775HCID 178485775, compound

Product 1

HCID 178485780HCID 178485780, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

287 mg (0.5 mmol) of (Z)-3-{1-[4-(N-phthalimidomethylcarbonyl-N-methylamino)phenylamino]-1-phenyl-methylidene}-5-nitro-2-indolinone are suspended in 20 ml of ethanol and 20 ml of dichloromethane and after the addition of 0.3 ml of 80% hydrazine hydrate solution stirred for 18 hours at 50° C. The mixture is then cooled to ambient temperature, the insoluble matter is suction filtered and the mother liquor is concentrated by evaporation. The residue is chromatographed on silica gel (dichloromethane/methanol/ammonia=92:8:0.8) and the product is again triturated with methanol, suction filtered and dried.

Workup

  1. temperatureThe mixture is then cooled to ambient temperature
  2. filtrationfiltered
  3. concentrationthe mother liquor is concentrated by evaporation
  4. customThe residue is chromatographed on silica gel (dichloromethane/methanol/ammonia=92:8:0.8)
  5. customthe product is again triturated with methanol, suction
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-2b5a4c8ab2a3437a9bdb9357e75d0e10
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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