Iodoethane → 2-cyano-3-(5-ethoxycarbonyl-1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamide

HRID 21546Notes

Reaction equation

HRID 21546 reaction equation
[C:1]([C:4]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:5]=1[CH2:6][C:7]1[C:11]([C:12](=[O:25])[CH:13]([C:23]#[N:24])[C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:15])=[N:10][N:9]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:8]=12)([OH:3])=[O:2].[CH2:36](I)[CH3:37].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:23]([CH:13]([C:12]([C:11]1[C:7]2[CH2:6][C:5]3[C:32](=[CH:33][CH:34]=[CH:35][C:4]=3[C:1]([O:3][CH2:36][CH3:37])=[O:2])[C:8]=2[N:9]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:10]=1)=[O:25])[C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15])#[N:24]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 199325603-(5-Carboxy-1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl)-2-cyano-3-oxo-N-phenyl-propanamide

Product 1

HCID 199326212-cyano-3-(5-ethoxycarbonyl-1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamideYield 77.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(5-Carboxy-1,4-dihydro-1-phenyl-indeno[1,2-c]pyrazol-3-yl)-2-cyano-3-oxo-N-phenyl-propanamide (2.3 g) dissolved in dimethylformamide (25 ml) is reacted with ethyl iodide (1.55 g) in the presence of anhydrous potassium carbonate (1.4 g) under stirring at room temperature for 2 hours. The reaction mixture is diluted with ice water and the precipitate is filtered, dissolved in chloroform and washed with 1N HCl and then with water. Evaporation of the solvent in vacuo gives a residue which is crystallized from CH2Cl2 /methanol to yield 1.9 g of 2-cyano-3-(5-ethoxycarbonyl-1,4-dihydro -1-phenyl-indeno[1,2-c]pyrazol-3-yl)-3-oxo-N-phenyl-propanamide, m.p. 233°-236° C. dec.

Workup

  1. filtrationthe precipitate is filtered
  2. dissolutiondissolved in chloroform
  3. washwashed with 1N HCl
  4. customEvaporation of the solvent in vacuo
  5. customgives a residue which
  6. customis crystallized from CH2Cl2 /methanol

Sources & evidence

ORD record
ord-0636a6b1d2a1493ba8579365dde00317
Source dataset
uspto-grants-1995_06
Patent number
US05424308

Reaction notes

Loading…