Dichloromethane → HCID 178486525, compound

HRID 1007457Notes

Reaction equation

HRID 1007457 reaction equation
[NH:1](/[C:8](=[C:17]1\[C:18](=[O:30])[NH:19][C:20]2[C:25]\1=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)/[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[N:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl>N.[Ni]>[NH:1](/[C:8](=[C:17]1\[C:18](=[O:30])[NH:19][C:20]2[C:25]\1=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)/[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH2:16])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 178486524HCID 178486524, compound

Product 1

HCID 178486525HCID 178486525, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

0.8 g of 3-(Z)-[1-anilino-1-(3-cyanophenyl)-methylidene]-5,6-dimethoxy-2-indolinone are dissolved in 50 ml of methanolic ammonia and 30 ml of methylene chloride are added. After the addition of 500 mg of Raney nickel the mixture is hydrogenated for 2 hours at ambient temperature at a pressure of 50 psi. After the end of the reaction the catalyst is filtered off and the filtrate is concentrated by evaporation. The residue is separated over a silica gel column with methylene chloride/methanol (5:1) as eluant. The product is suspended in 3 ml of dioxane, 0.4 ml of 1N hydrochloric acid are added and the solution formed is concentrated by evaporation after 10 minutes' stirring at ambient temperature. The residue thus obtained is triturated with ether, suction filtered and dried in vacuo at 80° C.

Workup

  1. customAfter the end of the reaction the catalyst
  2. filtrationis filtered off
  3. concentrationthe filtrate is concentrated by evaporation
  4. customThe residue is separated over a silica gel column with methylene chloride/methanol (5:1) as eluant
  5. addition0.4 ml of 1N hydrochloric acid are added
  6. customthe solution formed
  7. concentrationis concentrated by evaporation after 10 minutes'
  8. customThe residue thus obtained
  9. customis triturated with ether, suction
  10. filtrationfiltered
  11. customdried in vacuo at 80° C.

Sources & evidence

ORD record
ord-b247076ae6d84f0989bd9abfbe74ec94
Source dataset
uspto-grants-2004_09
Patent number
US06794395B1

Reaction notes

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