HCID 178418361, compound → HCID 178481040, compound

HRID 858305Notes

Reaction equation

HRID 858305 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[C:12]([NH:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([N:32]4[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]4)=[O:31])=[CH:26][CH:25]=3)[C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([N+:20]([O-])=O)[CH:14]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[H][H]>C(O)(=O)C.[Ni]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[C:12]([NH:23][C:24]3[CH:25]=[CH:26][C:27]([C:30]([N:32]4[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]4)=[O:31])=[CH:28][CH:29]=3)[C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([NH2:20])[CH:14]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178481041HCID 178481041, compound

Product 1

HCID 178481040HCID 178481040, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 176Acetic AcidSolvent

Procedure

0.746 g of 6-chloro-3-{1-[4-(4-methyl-1-piperazinyl-carbonyl)phenylamino]-1-(4-amino-3-nitrophenyl)methylene}-2-indolinone are hydrogenated in 30 ml acetic acid with the addition of 0.60 g Raney nickel under 50 psi of hydrogen pressure for 4 hours. After the addition of another 0.30 g of Raney nickel hydrogenation is continued under the same conditions for a further 4 hours, then the catalyst is removed by suction filtering. The residue obtained from the filtrate by distilling off the solvent is dissolved in water, the solution is made alkaline with soda solution. The crude product precipitated is suction filtered, washed with water, dried, dissolved in 70 ml of dichloromethane/methanol/ammonia solution=70:30:3 and filtered through a layer of silica gel. The filtrate is concentrated by evaporation, the residue is stirred with 5 ml of ethyl acetate, suction filtered and dried at 80° C.

Workup

  1. customthe catalyst is removed by suction
  2. filtrationfiltering
  3. customThe residue obtained from the filtrate
  4. distillationby distilling off the solvent
  5. dissolutionis dissolved in water
  6. customThe crude product precipitated
  7. filtrationfiltered
  8. washwashed with water
  9. customdried
  10. dissolutiondissolved in 70 ml of dichloromethane/methanol/ammonia solution=70:30:3
  11. filtrationfiltered through a layer of silica gel
  12. concentrationThe filtrate is concentrated by evaporation
  13. filtrationfiltered
  14. customdried at 80° C.

Sources & evidence

ORD record
ord-004743c9a1dd43ef9e73639f363203f4
Source dataset
uspto-grants-2006_12
Patent number
US07148249B2

Reaction notes

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