Reaction #684947

Reaction equation

4-n-butylbenzylchloride

dimethylformamide

sodium hydride

dimethylformamide

1-cyano-2-benzoyl-1,2-dihydroisoquinoline

→

aforementioned compound

Yield 17.2%

1-(4-butylbenzyl)isoquinoline

Yield 17.2%

Solvents

Water

Conditions

Workup

1. 1
   Concentrationthis was concentrated
2. 2
   workup.ADDITIONtoluene and water were added to this residue
3. 3
   WashThe toluene layer was washed with water
4. 4
   Dryingdried over potassium carbonate
5. 5
   Concentrationconcentrated
6. 6
   workup.ADDITIONTo an ethanol (1.6 ml) solution of the residue, 50% aqueous sodium hydroxide solution (0.63 ml) was added
7. 7
   Temperaturethis was refluxed for 2 hours
8. 8
   ConcentrationAfter concentration, toluene and water
9. 9
   workup.ADDITIONwere added
10. 10
    WashThe toluene layer was washed with water
11. 11
    Dryingdried over calcium carbonate
12. 12
    Concentrationconcentrated
13. 13
    OtherThe residue was purified by silica gel column chromatography

Procedure

To a dimethylformamide (1.8 ml) solution of 60% sodium hydride (16 mg, 0.40 mmol), a dimethylformamide (3.6 ml) solution of 1-cyano-2-benzoyl-1,2-dihydroisoquinoline (100 mg, 0.38 mmol) synthesized according to the literature of Org. Synth., VI, 115 (1988), and 4-n-butylbenzylchloride (70 mg, 0.38 mmol) was added dropwise under nitrogen atmosphere at −16° C., and was further stirred at room temperature for 30 minutes. Water was added, this was concentrated, and toluene and water were added to this residue. The toluene layer was washed with water, dried over potassium carbonate, and concentrated. To an ethanol (1.6 ml) solution of the residue, 50% aqueous sodium hydroxide solution (0.63 ml) was added, and this was refluxed for 2 hours. After concentration, toluene and water were added. The toluene layer was washed with water, then dried over calcium carbonate, and then concentrated. The residue was purified by silica gel column chromatography to give 18 mg of the aforementioned compound of the formula (Ia).

Source