تفاعل #59369

معادلة التفاعل

2-amino biphenyl

CO2

2-cyano-N-cyclopropylmethylacetamide

sodium acetate

sodium carbonate

hydrochloric acid

sodium nitrite

→

title compound

المردود 36.1%

2-(Biphenyl-2-yl-hydrazono)-2-cyano-N-cyclopropylmethyl-acetamide

المردود 36.1%

المذيبات

water

acetic acid

water

ethanol

water

water

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto maintain
2. 2
   درجة الحرارةwise maintaining an internal temperature of <5° C
3. 3
   workup.ADDITIONUpon complete addition
4. 4
   workup.STIRRINGthe reaction was stirred at 0° C. for 30 minutes
5. 5
   workup.ADDITIONpoured portion wise into a mechanically stirred 3-necked round bottomed flask
6. 6
   استخلاصextracted with ethyl acetate (400 mL)
7. 7
   غسيلThe organic layer was washed with water (200 mL) and brine (200 mL)
8. 8
   تجفيفdried over sodium sulfate
9. 9
   ترشيحThe mixture was filtered
10. 10
    تركيزconcentrated
11. 11
    أخرىpurified by recrystallization from ethyl acetate/hexanes

الإجراء التجريبي

To a stirred solution of 2-amino biphenyl (2.95 g, 17.4 mmol) in glacial acetic acid (16 mL) and water (14 mL) with cooling was added drop wise concentrated hydrochloric acid (10 mL). Additional water (10 mL) was added to maintain stirring. The mixture was cooled to 0° C. and a solution of sodium nitrite (1.44 g, 20.7 mmol) in water (10 mL) was added drop wise maintaining an internal temperature of <5° C. Upon complete addition, the reaction was stirred at 0° C. for 30 minutes, poured portion wise into a mechanically stirred 3-necked round bottomed flask charged with a predissolved solution of 2-cyano-N-cyclopropylmethylacetamide (2.8 g, 20.3 mmol), sodium acetate (12.0 g, 146 mmol), and sodium carbonate (12.8 g, 121 mmol) in 2:1 water: ethanol (180 mL). Vigorous CO2(g) evolution was observed. After 1 hour at 0° C., the reaction was diluted with water (200 mL) and extracted with ethyl acetate (400 mL). The organic layer was washed with water (200 mL) and brine (200 mL) and dried over sodium sulfate. The mixture was filtered, concentrated, and purified by recrystallization from ethyl acetate/hexanes to afford the title compound as a yellow solid (2.0 g, 36%). 1H NMR (500.133 MHz, CDCl3) δ 9.23 (t, J=5.3 Hz, 1H), 9.13 (bs, 1H), 8.43 (d, J=8.3 Hz, 1H), 8.17 (bs, 1H), 7.86 (d, J=7.2 Hz, 1H), 7.81 (t, J=7.6 Hz, 1H), 7.71 (d, J=7.5 Hz, 2H), 7.49 (t, J=7.2 Hz, 2H), 7.43 (t, J=7.2 Hz, 1H), 3.30 (s, 0H), 3.23 (t, J=6.1 Hz, 2H), 1.12 (septet, J=6.4 Hz, 1H), 0.45 (d, J=8.0 Hz, 2H), 0.29 (d, J=4.1 Hz, 2H). MS APCI, m/z=319 (M+H). HPLC 1.84 min.

المصدر