Chloroethane → HCID 13388143, compound

HRID 638011Notes

Reaction equation

HRID 638011 reaction equation
[CH3:1][C:2]1[C:10]([C:11](=[O:18])[C:12]2[CH2:17][CH2:16][CH2:15][NH:14][CH:13]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[H-].[Na+].[CH2:21](Cl)[CH3:22]>CN(C)C=O>[CH3:1][C:2]1[C:10]([C:11](=[O:18])[C:12]2[CH2:17][CH2:16][CH2:15][N:14]([CH2:21][CH3:22])[CH:13]=2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 6337ChloroethaneHCID 24758Sodium hydrideHCID 146826KC 764

Product 1

HCID 13388143HCID 13388143, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

One g of 2-methyl-3-(1,4,5,6-tetrahydronicotinoyl)pyrazolo[1,5-a]pyridine was dissolved in 20 ml of dimethyl-formamide and 0.3 g of sodium hydride (55%) was added whilst stirring to the mixture. The mixture was stirred at room temperature for 1 hour, and then 1 g of ethylchloride was added and stirred at 60° C. for 2 hours. After removal of solvent in vacuo, the residue was chromatographed over SiO2 employing CH2Cl2 --ethyl acetate--methanol (8:1.5:0.5) mixture as eluent. The eluate was evaporated to dryness in vacuo and the residue was recrystallized from benzene-hexane to afford the title compound in yield of 0.8 g (72%), mp. 104°-105° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. stirringstirred at 60° C. for 2 hours
  3. customAfter removal of solvent in vacuo
  4. customthe residue was chromatographed over SiO2
  5. customThe eluate was evaporated to dryness in vacuo
  6. customthe residue was recrystallized from benzene-hexane

Sources & evidence

ORD record
ord-ab199b9f41e24b40bbf9899bbed7d1d3
Source dataset
uspto-grants-1985_12
Patent number
US04559402

Reaction notes

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