Sodium hydride → HCID 15622460, compound

HRID 1199932Notes

Reaction equation

HRID 1199932 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:13]([C:15](=[C:18](OC)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16]#[N:17])#[N:14].[H-].[Na+]>CN(C)C=O>[C:13]([C:15]1[C:16](=[NH:17])[N:1]2[C:2]([CH:3]=[CH:4][CH:5]=[CH:6]2)=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)#[N:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75960Ethyl 2-pyridylacetateHCID 726895HCID 726895, compound

Product 1

HCID 15622460HCID 15622460, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2.50 g of ethyl 2-pyridylacetate and 2.79 g of 2-cyano-3-methoxy-3-phenylacrylonitrile was dissolved in 15 ml of dry N,N-dimethylformamide. To the solution was added 0.61 g of 60% sodium hydride and the reaction mixture was stirred for 1 hour at 60° C. The reaction mixture was poured into ice-water, and precipitated crystals were collected by filtration, washed with water and dried under vacuum to obtain 2.50 g of 3-cyano-1-ethoxycarbonyl-4-imino-2-phenyl-4H-quinolizine.

Workup

  1. customprecipitated crystals
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-db8e27a7150b4c7480306b77ca1e8c23
Source dataset
uspto-grants-1990_02
Patent number
US04904657

Reaction notes

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