تفاعل #40658

معادلة التفاعل

Aniline

3-methylbut-2-enoyl chloride

→

1a

4,4-Dimethyl-3,4-dihydro-1H-quinolin-2-one

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux for 2 h
2. 2
   درجة الحرارةAfter cooling
3. 3
   ترشيحthe mixture was filtered
4. 4
   تركيزThe filtrate was concentrated to dryness
5. 5
   أخرىdried under vacuum
6. 6
   workup.DISSOLUTIONThe crude 3-methyl-but-2-enoic acid phenylamide (ca. 10 g) was dissolved in toluene (50 mL)
7. 7
   workup.ADDITIONThis toluene solution was added to the stirred AlCl3 powder (27 g) portion-wise
8. 8
   workup.ADDITIONAfter addition
9. 9
   workup.ADDITIONThe warm slurry was poured carefully
10. 10
    استخلاصThe resulting mixture was extracted with EtOAc (3×)
11. 11
    غسيلwashed with sat'd NaHCO3, H2O, brine
12. 12
    تجفيفdried over MgSO4
13. 13
    أخرىThe residue was purified by silica gel flash chromatography (CH2Cl2

الإجراء التجريبي

Aniline (7.26 g, 45.2 mmol) and 3-methylbut-2-enoyl chloride (53.2 g, 45.2 mmol) were heated in chloroform at reflux for 2 h. After cooling, the mixture was filtered. The filtrate was concentrated to dryness and dried under vacuum. The crude 3-methyl-but-2-enoic acid phenylamide (ca. 10 g) was dissolved in toluene (50 mL). This toluene solution was added to the stirred AlCl3 powder (27 g) portion-wise. After addition, the resulting dark brown solution was heated at 80° C. for 2.5 h. The warm slurry was poured carefully to stirred crashed ice. The resulting mixture was extracted with EtOAc (3×), washed with sat'd NaHCO3, H2O, brine, and dried over MgSO4. The residue was purified by silica gel flash chromatography (CH2Cl2, then EtOAc) to give 2.2 g of pure 1a and about 4-5 g of less pure portion 1a. LC-MS ESI 176 (M+H).

المصدر