تفاعل #812307

معادلة التفاعل

methyl 6-aminohexanoate hydrochloride

triethylamine

2-acetoxy-3-methoxybenzoyl chloride

→

title compound

المردود 55.0%

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

المردود 55.0%

المذيبات

benzene

benzene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةunder reflux for 2 hours
2. 2
   workup.STIRRINGwhile stirring
3. 3
   درجة الحرارةthe reaction mixture was cooled down
4. 4
   ترشيحthe precipitate was filtered by suction
5. 5
   أخرىthe filtrate was evaporated 20 ml of water
6. 6
   workup.ADDITIONwere portionwise added to the residue
7. 7
   استخلاصthe solution was extracted with ethyl acetate
8. 8
   غسيلthe organic phase was washed with 1M hydrochloric acid and water
9. 9
   أخرىdried
10. 10
    أخرىThe solvent was evaporated under reduced pressure
11. 11
    أخرىThe residue was purified by chromatography on a silica gel column
12. 12
    workup.ADDITIONa 3:4 mixture of petroleum ether and ethyl acetate

الإجراء التجريبي

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.

المصدر