Ammonia → HCID 178465945, compound

HRID 347996Notes

Reaction equation

HRID 347996 reaction equation
C([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](OCC)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]1=[O:26])(=O)C.[CH3:27][N:28]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=1)[CH3:29].N>CN(C)C=O>[C:13]([C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][C:5](=[O:26])[C:6]2=[C:16]([NH:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][N:28]([CH3:27])[CH3:29])=[CH:36][CH:35]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 308051Benzenemethanamine, 4-amino-N,N-dimethyl-HCID 689919611,5-Diacetyl-3-(ethoxy-phenyl-methylidene)-2-indolinone

Product 1

HCID 178465945HCID 178465945, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

200 mg (0.57 mmol) 1,5-diacetyl-3-[ethoxy-phenyl-methylidene]-2-indolinone (Ex. III) are suspended in 5 ml of dimethylformamide and stirred with 86 mg 0.57 mmol) 4-dimethylaminomethyl-phenylamine at an ambient temperature of 80° C. for about 5 h. The acetyl-protected intermediate product is combined with 2 ml of conc. ammonia without being purified and stirred overnight at ambient temperature. Then the mixture is evaporated down and the residue is chromatographed through a silica gel column with methylene chloride/methanol 9:1 as eluant.

Workup

  1. customwithout being purified
  2. customThen the mixture is evaporated down
  3. customthe residue is chromatographed through a silica gel column with methylene chloride/methanol 9:1 as eluant

Sources & evidence

ORD record
ord-3bb3636a2cd04ddba22d2730f126c71e
Source dataset
uspto-grants-2007_02
Patent number
US07176231B2

Reaction notes

Loading…