Ammonia → HCID 53698256, compound

HRID 1578378Notes

Reaction equation

HRID 1578378 reaction equation
N.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:12][C:13]#[N:14])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11].Cl[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[CH:18][CH:17]=1>>[N:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:16]([CH:12]([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH3:2])[CH:5]=2)[C:13]#[N:14])=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 667273,4-DimethoxybenzeneacetonitrileHCID 691404-Chloroquinoline

Product 1

HCID 53698256HCID 53698256, compound

Procedure

To 500 ml of liquid NH3 was added 35.4 g (0.2 mol) of 3,4-dimethoxyphenylacetonitrile and 11.7 g (0.3 mol) of NaNH2. The mixture was stirred for two hours, maintaining a temperature at -25° to -30°C by cooling in a dry ice/acetone bath. 4-Chloroquinoline (16.4 g, 0.1 mol) was added and the resulting mixture was allowed to stir at room temperature until all excess NH3 had evaporated. Benzene was added to the residue and water was added slowly to destroy excess NaNH2. The phases were separated and the aqueous phase was extracted with benzene. The combined benzene extracts were extracted with 9M HCl (2×150 ml). The acidic phase was washed with Et2O (500 ml), cooled and basified with concentrated NH4OH. The aqueous mixture was extracted with CHCl3 (500 ml). The CHCl3 extract was dried with MgSO4 and evaporated to give a quantitative yield of crude α-(4 -quinolinyl)-α-(3,4-dimethoxyphenyl)acetonitrile intermediate.

Workup

  1. temperaturemaintaining a temperature at -25° to -30°C
  2. temperatureby cooling in a dry ice/acetone bath
  3. customhad evaporated
  4. additionBenzene was added to the residue and water
  5. additionwas added slowly
  6. customto destroy excess NaNH2
  7. customThe phases were separated
  8. extractionthe aqueous phase was extracted with benzene
  9. extractionThe combined benzene extracts were extracted with 9M HCl (2×150 ml)
  10. washThe acidic phase was washed with Et2O (500 ml)
  11. temperaturecooled
  12. extractionThe aqueous mixture was extracted with CHCl3 (500 ml)
  13. extractionThe CHCl3 extract
  14. dry with materialwas dried with MgSO4
  15. customevaporated

Sources & evidence

ORD record
ord-ed01b8a76ed1452aa655aa9636445c0d
Source dataset
uspto-grants-1976_02
Patent number
US03936461

Reaction notes

Loading…