Hydrochloric Acid → HCID 67517935, compound

Participants

Reaction Steps

Methyl 2-(1H-tetrazol-1-yl)-5,6,7,8-tetrahydroquinoline-5-carboxylate (1.04 g, 4.01 mmol) and lithium hydroxide (0.202 g, 4.81 mmol) were stirred in a mixture of tetrahydrofuran (10 ml)/water (10.00 ml) for 75 mins. The tlc showed some 20% starting material so more LiOH (50 mg, 1.19 mmol) was added and stirred for another 1 hr. The reaction was adjusted with 2N HCl (3 ml, 6 mmol) to pH 4-5 then extracted with ethyl acetate 2×. The ethyl acetate layers were combined and dried over Na2SO4, filtered and evaporated to dryness to yield 2-(1H-tetrazol-1-yl)-5,6,7,8-tetrahydroquinoline-5-carboxylic acid. 1H-NMR (600 MHz, CDCl3): δ ppm 9.53 (s, 1H), 7.85-7.89 (q, 2H), 3.945 (t, J=5.46 Hz, 1H), 3.01-3.05 (m, 1H), 2.90-2.96 (m, 1H), 2.29-2.44 (m, 1H), 2.04-2.13 (m, 2H), 1.95-2.01 (m, 1H); LC-MS: (M+1)-28=218.

Provenance & Evidence