Methanol → HCID 178465946, compound

HRID 855768Notes

Reaction equation

HRID 855768 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=2)[C:6](=[C:16]([C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=2)[NH:17][CH:18]2[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]2)[C:5]1=[O:34])(=[O:3])[CH3:2].CO.C(OCC)(=O)C.CN(C)C=O>O1CCCC1.[Ni]>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=2)[C:6](=[C:16]([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[NH:17][CH:18]2[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]2)[C:5]1=[O:34])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 178465947HCID 178465947, compound

Product 1

HCID 178465946HCID 178465946, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2.4 g (5 mmol) 1,5-diacetyl-3-[4-nitrophenyl-(1-methyl-piperidin-4-ylamino)-methylidene]-2-indolinone are dissolved in 40 ml of tetrahydrofuran (THF), 30 ml of methanol and 30 ml of ethyl acetate, combined with 250 mg Raney nickel and hydrogenated for 6 h at ambient temperature at a pressure of 50 psi. Then 20 ml of dimethylformamide are added in order to dissolve the precipitate formed and hydrogenation is continued for 2 h. Then the catalyst is filtered off and the solution is evaporated down.

Workup

  1. dissolutionto dissolve the precipitate
  2. customformed
  3. filtrationThen the catalyst is filtered off
  4. customthe solution is evaporated down

Sources & evidence

ORD record
ord-9aaeaef1623c44acbda20be7a58bcbe4
Source dataset
uspto-grants-2007_08
Patent number
US07262206B2

Reaction notes

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