تفاعل #45376

معادلة التفاعل

3-bromoacetophenone

formamide

→

1-(3-bromophenyl)ethanamine

المذيبات

formic acid

ظروف التفاعل

المعالجة

1. 1
   أخرىThe brown liquid obtained
2. 2
   درجة الحرارةwas cooled to RT
3. 3
   أخرىquenched with water
4. 4
   استخلاصextracted with ethyl acetate
5. 5
   غسيلThe organic layer was washed with water, brine
6. 6
   تركيزconcentrated
7. 7
   workup.DISSOLUTIONThe resulting brown liquid was dissolved in ethanol (375 mL)
8. 8
   درجة الحرارةconc. HCl (75 mL) and the mixture was refluxed over night
9. 9
   أخرىEthanol was removed completely
10. 10
    غسيلthe aqueous layer was washed with ether and ethyl acetate
11. 11
    أخرىto remove all non-basic impurities
12. 12
    استخلاصextracted with ethyl acetate
13. 13
    غسيلThe ethyl acetate layer was washed with brine
14. 14
    تركيزconcentrated
15. 15
    أخرىto provide 26 g (86.65%) of A56.1
16. 16
    أخرىThis compound was taken to the next step with out further purification

الإجراء التجريبي

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.

المصدر