Benzylamine → HCID 178516089, compound

Participants

Reaction Conditions

Reaction Steps

6-Chloro-2-pyridinol (6.1 g, 0.047 mole) and 10.1 g (0.094 mole) of benzylamine were mixed and heated in an oil bath at 120°-130° for 48 hours. The liquid mass gradually solidified. The cooled mixture was boiled with 100 ml of 50% aqueous ethanol and cooled to 25° C.; the supernatant was decanted from a gum (which was saved), cooled to 5° C., decanted from black tar, and diluted with 50 ml of water. A grey, granular solid, m.p. 158°-162° C., crystallized. An additional quantity of the same material was recovered as follows: The retained gum was digested with 50 ml of hot 95% ethanol until it was solid; the mixture was cooled to 5° C., the solid removed, and the filtrate diluted with water. The total yield of the title compound was 2.4 g (25%). Recrystallization from benzene-n-hexane raised the m.p. to 164°-165°. 1H nmr (CDCl3 +D2O, 100 MHz), δ4.28 (s, 2H, CH2), 5.28 (d, 1H, H5, J=8 Hz), 5.50 (d, 1H, H3, J=9 Hz), 7.17 (t, 1H, H4, J=8 Hz), 7.30 (s, 5H, C6H5).

Provenance & Evidence