Reacción #6697

Ecuación de reacción

3-chloroaniline

1,3,3-trimethoxybutane

→

desired product

7-chlorolepidine

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropreheated to 60° C.
2. 2
   TemperaturaThe resulting mixture was refluxed for two hours
3. 3
   OtroThe volatile matrials were then removed in vacuo
4. 4
   OtroThe resulting mixture was partitioned between water and diethyl ether (3 times)
5. 5
   SecadoThe combined ether layer was dried over magnesium sulfate
6. 6
   OtroRotary evaporation of the ether solution
7. 7
   Otrogave a dark liquid
8. 8
   workup.ADDITIONThe liquid was added to a silica gel column
9. 9
   Lavadoeluted with hexane/ethyl acetate (3:1)

Procedimiento

To a mixture containing 3-chloroaniline (1.59 g), ferric chloride hexahydrate (5.4 g), zinc chloride (0.2 g), ethanol (20 ml of 95% aqueous solution) preheated to 60° C. was added 1,3,3-trimethoxybutane (1.48 g). The resulting mixture was refluxed for two hours and allowed to stand overnight. The volatile matrials were then removed in vacuo and the residue rendered basic with 10% aqueous sodium hydroxide. The resulting mixture was partitioned between water and diethyl ether (3 times). The combined ether layer was dried over magnesium sulfate. Rotary evaporation of the ether solution gave a dark liquid. The liquid was added to a silica gel column and eluted with hexane/ethyl acetate (3:1) to give the desired product as tan crystals.

Fuente