Ammonium Chloride → 6-Phenoxy-3-[1-(tetrahydro-pyran-4-yl)-pent-4-enyl]-quinolin-2-ylamine

Participants

Reaction Steps

To the oil isolated in Step B (23.28 g, 70.7 mmol) in THF (100 mL) at −78° C., LHDMS (1.0 M, 84.8 mL, 84.8 mmol) was added slowly. The reaction mixture was then stirred at room temperature for 1 hour. A solution of 2-nitro-5-phenoxybenzaldehyde (20.63 g, 75.5 mmol) in THF (100 mL) was added. The reaction mixture was stirred at room temperature overnight. Saturated aqueous ammonium chloride (200 mL) was added. The reaction mixture was extracted with ethyl acetate three times. The combined organic extracts were washed with brine and dried over magnesium sulfate. The reaction mixture was filtered and concentrated to yield a colorless oil which was a mixture of cis-[2-(2-nitro-5-phenoxy-benzylidene)-3-(tetrahydro-pyran-4-yl)-hept-6-enenitrile] and trans-[2-(2-nitro-5-phenoxy-benzylidene)-3-(tetrahydro-pyran-4-yl)-hept-6-enenitrile].

Provenance & Evidence