Intensain,Hoechst,Switz,1963
ChEBI: Carbocromen hydrochloride is a member of coumarins.
18.7 g of 3β-diethylaminoethyl-4-methyl-7-hydroxy-coumarin chlorhydrate are
dissolved in 200 cc methyl ethyl ketone and 18 g anhydrous potassium
carbonate are added. The mixture is stirred for 1 hour at 70°C and then 12 g
bromoacetic acid ethyl ester are allowed to drop in. The reaction mixture is
stirred under reflux for 9 hours and then it is filtered off with suction in the
heat. The filtrate is concentrated in the vacuum to dryness and the resultant
residue is dissolved in ether. The etheric solution is washed with diluted
caustic soda solution for several times and, subsequently, dried with Glauber's
salt. By introduction of hydrochloric acid gas into the etheric solution the
reaction product is precipitated in the form of chlorhydrate. Yield: 15 g of 3β-
diethylaminoethyl-4-methylcoumarin-7-ethyl oxyacetate chlorhydrate having a
melting point of 154° to 156°C (= 63% of the theory).
The starting material is produced by reacting resorcinol with 2-(2-
diethylaminoethyl)acetic acid ethyl ester.
