Hydrogen Bromide → HCID 20373065, compound

Participants

Reaction Steps

A solution of 184 ml. of phosphorus oxychloride in 180 ml. of chloroform is added dropwise, with stirring, to a solution of 235 g. of 1-(2-hydroxyethyl)-3-hydroxy-1,2,3,4-tetrahydroquinoline (an oil, hydrobromide, m.p. 167°), obtainable by dropwise addition of 2-anilinoethanol to a solution of epichlorohydrin in isopropanol, boiling for 4 hours, evaporating and heating the residue at 160° for 3 hours in diethylaniline/cyclohexanol, in 355 ml. of chloroform. The mixture is boiled for 2 hours more and cooled. Excess phosphorus oxychloride is decomposed by adding 600 ml. of water dropwise. The phases are separated and the aqueous phase is extracted several times with chloroform, washed with water until neutral and evaporated to give 1-(2-chloroethyl)-2-chloromethylindoline hydrochloride, an oil, which is converted directly to the free base, b.p. 132°-135°/0.05 mm.

Provenance & Evidence