Pyridine → HCID 86738111, compound

Participants

Reaction Steps

3.77 ml (40 mmol) of acetic anhydride are added dropwise to a stirred mixture of 5.19 g (20 mmol) of octahydro-4a-(3-hydroxyphenyl)-2-methyl-cis-6(2H)-isoquinoline (see Example 3), 3.22 ml (40 mmol) of pyridine and 20 ml of toluene at 5°. The mixture is then kept at 22° for 2 hours. 20 ml of water is added to the mixture at 5°, and the mixture is stirred for 30 minutes at 22°. 40 ml of methylene chloride are added. Whilst being stirred, the aqueous phase of the resultant twophase mixture is adjusted to pH 7 by the addition of 4 g of sodium carbonate. The aqueous phase is then separated and extracted with methylene chloride. The organic phases are washed with water, dried, concentrated by evaporation and dried in a high vacuum. The title compound is obtained as a viscous oil which is crystallized as the hydrogen fumarate from isopropanol; M.Pt. 194° (decomposition).

Provenance & Evidence