Реакция #45376

Уравнение реакции

3-bromoacetophenone

formamide

→

1-(3-bromophenyl)ethanamine

Растворители

formic acid

Условия реакции

Обработка

1. 1
   ДругоеThe brown liquid obtained
2. 2
   Температураwas cooled to RT
3. 3
   Другоеquenched with water
4. 4
   Экстракцияextracted with ethyl acetate
5. 5
   ПромывкаThe organic layer was washed with water, brine
6. 6
   Концентрированиеconcentrated
7. 7
   workup.DISSOLUTIONThe resulting brown liquid was dissolved in ethanol (375 mL)
8. 8
   Температураconc. HCl (75 mL) and the mixture was refluxed over night
9. 9
   ДругоеEthanol was removed completely
10. 10
    Промывкаthe aqueous layer was washed with ether and ethyl acetate
11. 11
    Другоеto remove all non-basic impurities
12. 12
    Экстракцияextracted with ethyl acetate
13. 13
    ПромывкаThe ethyl acetate layer was washed with brine
14. 14
    Концентрированиеconcentrated
15. 15
    Другоеto provide 26 g (86.65%) of A56.1
16. 16
    ДругоеThis compound was taken to the next step with out further purification

Методика

A mixture of commercially available 3-bromoacetophenone (30 g, 0.1508 mol), formic acid (47 mL) and formamide (70 mL) was heated to 220° C. for 5 h. The brown liquid obtained was cooled to RT, quenched with water and extracted with ethyl acetate. The organic layer was washed with water, brine and concentrated. The resulting brown liquid was dissolved in ethanol (375 mL) and conc. HCl (75 mL) and the mixture was refluxed over night. Ethanol was removed completely and the aqueous layer was washed with ether and ethyl acetate to remove all non-basic impurities. The aqueous layer was basified with a 10% aqueous sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, and concentrated to provide 26 g (86.65%) of A56.1. This compound was taken to the next step with out further purification. 1H NMR (CDCl3, 300 MHz) δ 1.38 (d, 3H), 4.1 (q, 1H), 7.2 (m, 1H), 7.27 (m, 1H), 7.37 (m, 1H), 7.51 (s, 1H). LS-MS (M−H)+=200.

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