1,2,3,4-tetrahydro-8-Quinolinecarbonitrile synthesis
- Product Name:1,2,3,4-tetrahydro-8-Quinolinecarbonitrile
- CAS Number:50741-37-2
- Molecular formula:C10H10N2
- Molecular Weight:158.2
Yield:50741-37-2 68%
Reaction Conditions:
with boron trichloride;potassium carbonate in methanol;dichloromethane;toluene;
Steps:
74 EXAMPLE 74
EXAMPLE 74 To a solution of 1.33 g of 1,2,3,4-tetrahydroquinoline in 10 ml of toluene was added 5.5 ml of a solution of 2.02M of boron trichloride in toluene under ice-cooling. The mixture was refluxed on an oil bath for 1 hr. and evaporated under atmospheric pressure to remove the toluene. The residue was mixed with 2 ml of trichloroacetonitrile and heated at 60°-62° C. on an oil bath for 20 hr. The reaction mixture was dissolved in 20 ml of methylene chloride and poured into a mixture of 9.1 g of potassium carbonate and 40 ml of methanol under ice-cooling. The mixture was refluxed on an oil bath for 1 hr. and filtered to remove the insoluble material. The filtrate was concentrated and partitioned between water and methylene chloride. The methylene chloride layer was washed with dilute HCl, dried over anhydrous magnesium sulfate and concentrated to remove the solvent. The residue (1.53 g) was purified on a Lobar column and the product (1.10 g) from the methylene chloride elude was recrystallized from ether-n-hexane to give 1.07 g of 8-cyano-1,2,3,4-tetrahydroquinoline as crystals melting at 75°-76° C. Yield: 68%
References:
US4774331,1988,A
35509-27-4
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50741-37-2
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