Acetic Acid → 1-Benzyl-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-benzyl-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbaldehyde (45 mg, 0.17 mmol) from step 3 in acetic acid (0.38 mL, 6.6 mmol) was added nitroethane (0.24 mL, 3.4 mmol) and sodium acetate (270 mg, 3.4 mmol). The reaction mixture was heated at a sealed tube at 115° C. overnight. Added some water and extracted it with ether. Combined organic layer and evaporated under vacuum. It was purified by prep TLC eluting with 10% ethyl acetate-hexane and providing 20 mg (45%) of the title compound. 1H-NMR (CDCl3) δ 7.36–7.21 (m, 3H), 7.18–7.14 (m, 2H), 6.99 (s, 1H), 5.98 (s, 1H), 4.48 (s, 2H), 3.41 (t, J=5.7 Hz, 2H), 2.70 (t, J=6.4 Hz, 2H), 1.97 (m, 2H).

Provenance & Evidence