Реакция #40658

Уравнение реакции

Aniline

3-methylbut-2-enoyl chloride

→

1a

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

Растворители

chloroform

Условия реакции

Обработка

1. 1
   Температураat reflux for 2 h
2. 2
   ТемператураAfter cooling
3. 3
   Фильтрацияthe mixture was filtered
4. 4
   КонцентрированиеThe filtrate was concentrated to dryness
5. 5
   Другоеdried 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
    ЭкстракцияThe resulting mixture was extracted with EtOAc (3×)
11. 11
    Промывкаwashed with sat'd NaHCO3, H2O, brine
12. 12
    Сушкаdried over MgSO4
13. 13
    ДругоеThe residue was purified by silica gel flash chromatography (CH2Cl2

Методика

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).

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