Dichloromethane → 2-Benzoyl-1-cyano-5,7-dibenzyloxy-1,2-dihydroisoquinoline

HRID 973039Notes

Reaction equation

HRID 973039 reaction equation
[C-:1]#[N:2].[K+].C(Cl)Cl.[CH2:7]([O:14][C:15]1[CH:24]=[C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][N:19]=[CH:20]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O.CCOCC>[C:33]([N:19]1[CH:18]=[CH:17][C:16]2[C:21](=[CH:22][C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:24][C:15]=2[O:14][CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:20]1[C:1]#[N:2])(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 9032Potassium CyanideHCID 127070595,7-Bis(benzyloxy)isoquinoline

Product 1

HCID 127070612-Benzoyl-1-cyano-5,7-dibenzyloxy-1,2-dihydroisoquinolineYield 87.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3 g of potassium cyanide in 15 ml of water is added to 25 ml of a methylene chloride solution containing 3.3 g of 5,7-dibenzyloxyisoquinoline. 6.4 g of benzoyl chloride are added to the mixture at 0° C for 2 hours under stirring. After the mixture is allowed to stand at room temperature, the methylene chloride layer is separated therefrom. The methylene chloride solution separated is washed with an aqueous 1% sodium hydroxide solution and water, respectively. The methylene chloride solution is then dried and evaporated to remove solvent. The oily residue thus obtained is dissolved in 10 ml of ether, and this solution is poured onto a silica gel column. The column is eluted with a mixture of ether and hexane. The eluate is evaporated to remove solvent, and the crystalline residue thus obtained is recrystallized from ethanol. 4 g of 2-benzoyl-1-cyano-5,7-dibenzyloxy-1,2-dihydroisoquinoline are thereby obtained. Yield: 64% M.p. 123° - 125° C.

Workup

  1. customto stand at room temperature
  2. customthe methylene chloride layer is separated
  3. customThe methylene chloride solution separated
  4. washis washed with an aqueous 1% sodium hydroxide solution and water
  5. dry with materialThe methylene chloride solution is then dried
  6. customevaporated
  7. customto remove solvent
  8. customThe oily residue thus obtained
  9. additionthis solution is poured onto a silica gel column
  10. washThe column is eluted with a mixture of ether and hexane
  11. customThe eluate is evaporated
  12. customto remove solvent
  13. customthe crystalline residue thus obtained
  14. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-099dffb0c9014217869eaeecc43dd270
Source dataset
uspto-grants-1977_10
Patent number
US04054659

Reaction notes

Loading…