4'-Cyanoacetophenone → HCID 54172885, compound

HRID 2073879Notes

Reaction equation

HRID 2073879 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=1)=[O:3].[N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[CH2:22][O:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH:27]=O.[O-]CC.[Na+]>C(O)C>[N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][C:13]=1[CH2:22][O:23][C:24]1[CH:25]=[C:26]([CH:27]=[CH:1][C:2]([C:4]2[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=2)=[O:3])[CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 740444'-CyanoacetophenoneHCID 2723922Sodium ethoxideHCID 10422857HCID 10422857, compound

Product 1

HCID 54172885HCID 54172885, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Cyano acetophenone (0.01 mol) in ethanol (100 ml) is added dropwise to a 0° C. mixture of 3-(2-quinolinylmethyloxy)benzaldehyde (0.01 mol) and sodium ethoxide (0.001 mol) in ethanol (200 ml). The reaction mixture is allowed to thaw to ambient temperature and after several hours it is evaporated and partitioned between ethyl acetate and water. The ethyl acetate fraction is dried and evaporated to give 4-(3-(3-(2-quinolinylmethyloxy)phenyl)-1-oxo-2-propen-1-yl)-benzonitrile.

Workup

  1. customthaw to ambient temperature
  2. customafter several hours it is evaporated
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe ethyl acetate fraction is dried
  5. customevaporated

Sources & evidence

ORD record
ord-448ff5b3f5a344d191354f9830004beb
Source dataset
uspto-grants-1990_04
Patent number
US04920133

Reaction notes

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