反応 #812307

反応方程式

methyl 6-aminohexanoate hydrochloride

triethylamine

2-acetoxy-3-methoxybenzoyl chloride

→

title compound

収率 55.0%

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

収率 55.0%

溶媒

benzene

benzene

反応条件

後処理

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

実験手順

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.

出典