반응 #735277

반응 방정식

4-(4-chloro-2-fluorobenzyl)-2-methyl-1,2,3,4-tetrahydro-4-isoquinolinol

sodium hydride

→

product

수율 129.1%

6-Chloro-2'-methylspiro[benzofuran-2(3H),4'(2'H)-isoquinoline] hydrochloride

수율 129.1%

용매

toluene

dimethylformamide

water

ether

반응 조건

후처리

1. 1
   세척previously washed with hexane, in toluene (65 ml)
2. 2
   workup.ADDITIONAfter the addition
3. 3
   온도to reflux
4. 4
   workup.ADDITIONdimethylformamide (35 ml) is slowly added dropwise
5. 5
   온도The reaction mixture is heated
6. 6
   온도under reflux for four hours
7. 7
   기타Removal of the solvents
8. 8
   기타yields an oil which
9. 9
   추출extracted with chloroform
10. 10
    세척The combined organic extracts are washed with water, saturated sodium chloride solution
11. 11
    건조dried over anhydrous magnesium sulfate
12. 12
    여과After filtering
13. 13
    기타removal of the solvent
14. 14
    기타yields an oil which
15. 15
    기타The salt is recrystallized from ethyl acetate/methanol

실험 절차

A solution of 4-(4-chloro-2-fluorobenzyl)-2-methyl-1,2,3,4-tetrahydro-4-isoquinolinol (10.0 g) in toluene (65 ml) and dimethylformamide (10 ml) is added dropwise to a suspension of sodium hydride (50%, 3.2 g), previously washed with hexane, in toluene (65 ml). After the addition is complete, the mixture is brought to reflux and dimethylformamide (35 ml) is slowly added dropwise. The reaction mixture is heated under reflux for four hours. Removal of the solvents yields an oil which is stirred in water (500 ml) and extracted with chloroform. The combined organic extracts are washed with water, saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering, removal of the solvent yields an oil which is dissolved in ether and converted to the product hydrochloride salt. The salt is recrystallized from ethyl acetate/methanol to yield the product as a white solid (6.8 g, 60%), mp 196°-199°. An analytical sample is twice recrystallized to yield a white solid, mp 200.5°-202° (dec.).

출처