Reaction #6697

Reaction equation

3-chloroaniline

1,3,3-trimethoxybutane

→

desired product

7-chlorolepidine

Solvents

ethanol

Conditions

Workup

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

Procedure

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.

Source