Benzaldehyde → (Z)-tert-Butyl-7-(1-cyano-2-phenylvinyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

HRID 2167440Notes

Reaction equation

HRID 2167440 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18][C:19]#[N:20])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[O-].[Na+].[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12](/[C:18](/[C:19]#[N:20])=[CH:25]/[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 2723922Sodium ethoxideHCID 66978184tert-Butyl-7-(cyanomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 66978138(Z)-tert-Butyl-7-(1-cyano-2-phenylvinyl)-3,4-dihydroisoquinoline-2(1H)-carboxylateYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 0.231 mmol tert-butyl-7-(cyanomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate in 2 ml ethanol were added 0.278 mmol of NaOEt solution (21%) and 0.254 mmol benzaldehyde. The mixture was stirred at room temperature over night. The mixture was diluted with ethanol and H2O, and a white precipitation observed. The solid was filtered off and washed with ethanol and H2O. The white solid was dissolved in methanol. Evaporation of the solvent gave 64 mg (77%) of solid material.

Workup

  1. customa white precipitation
  2. filtrationThe solid was filtered off
  3. washwashed with ethanol and H2O
  4. dissolutionThe white solid was dissolved in methanol
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ce179c09b6b148219475ad9df97e73e2
Source dataset
uspto-grants-2015_06
Patent number
US09045459B2

Reaction notes

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