반응 #812307

반응 방정식

methyl 6-aminohexanoate hydrochloride

triethylamine

2-acetoxy-3-methoxybenzoyl chloride

→

title compound

수율 55.0%

methyl 6-[N-(2 -hydroxy-3-methoxybenzoyl)amino]hexanoate

수율 55.0%

용매

benzene

benzene

반응 조건

후처리

1. 1
   온도under reflux for 2 hours
2. 2
   workup.STIRRINGwhile stirring
3. 3
   온도the reaction mixture was cooled down
4. 4
   여과the precipitate was filtered by suction
5. 5
   기타the filtrate was evaporated 20 ml of water
6. 6
   workup.ADDITIONwere portionwise added to the residue
7. 7
   추출the solution was extracted with ethyl acetate
8. 8
   세척the organic phase was washed with 1M hydrochloric acid and water
9. 9
   기타dried
10. 10
    기타The solvent was evaporated under reduced pressure
11. 11
    기타The residue was purified by chromatography on a silica gel column
12. 12
    workup.ADDITIONa 3:4 mixture of petroleum ether and ethyl acetate

실험 절차

2.3 g (10 mmol) of 2-acetoxy-3-methoxybenzoyl chloride dissolved in 18 ml of anhydrous benzene were dropwise added to the suspension of 1.80 g (10 mmol) methyl 6-aminohexanoate hydrochloride in 2.2 g (22 mmol) of anhydrous triethylamine and 18 ml of anhydrous benzene under nitrogen at room temperature while stirring. After boiling under reflux for 2 hours while stirring, the reaction mixture was cooled down, the precipitate was filtered by suction and the filtrate was evaporated 20 ml of water were portionwise added to the residue, the solution was extracted with ethyl acetate, the organic phase was washed with 1M hydrochloric acid and water, then dried. The solvent was evaporated under reduced pressure. The residue was purified by chromatography on a silica gel column by using a 3:4 mixture of petroleum ether and ethyl acetate to obtain 1.62 g (55%) of the title compound, m.p.: 69°-70° C.

출처