Reacción #812307

Ecuación de reacción

methyl 6-aminohexanoate hydrochloride

triethylamine

2-acetoxy-3-methoxybenzoyl chloride

→

title compound

Rendimiento 55.0%

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

Rendimiento 55.0%

Disolventes

benzene

benzene

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente