تفاعل #314909

معادلة التفاعل

2-Fluoro-N-(3-fluoro-phenyl)-5-nitro-benzamide

hydrazine monohydrate

→

title compound

المردود 64.3%

(3-Fluoro-phenyl)-(5-nitro-1H-indazol-3-yl)-amine

المردود 64.3%

المذيبات

EtOH

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   درجة الحرارةat reflux for 5 minutes
3. 3
   أخرىa yellow solid was precipitated out
4. 4
   درجة الحرارةto cool to room temperature
5. 5
   ترشيحthe solid was filtered off
6. 6
   workup.DISSOLUTIONThe solid was dissolved in phosphorous oxychloride (40 mL)
7. 7
   درجة الحرارةthe mixture heated at 90° C. for 1.5 hr
8. 8
   درجة الحرارةto cool to room temperature
9. 9
   تركيزThe reaction mixture was concentrated
10. 10
    أخرىpartitioned between EtOAc and saturated sodium bicarbonate
11. 11
    تجفيفThe organic phase was dried over MgSO4
12. 12
    تركيزconcentrated

الإجراء التجريبي

2-Fluoro-N-(3-fluoro-phenyl)-5-nitro-benzamide (1.1 μg, 4 mmol) was suspended in EtOH (25 mL) and the mixture heated to ˜60° C. To the resulting solution was added hydrazine monohydrate (1.06 mL, 20 mmol). The mixture was heated at reflux for 5 minutes and a yellow solid was precipitated out. The mixture was allowed to cool to room temperature then the solid was filtered off. The solid was dissolved in phosphorous oxychloride (40 mL) and the mixture heated at 90° C. for 1.5 hr then allowed to cool to room temperature and stirred for overnight. The reaction mixture was concentrated and partitioned between EtOAc and saturated sodium bicarbonate. The organic phase was dried over MgSO4 and concentrated to afford the title compound as a red solid (0.7 g, 64%). MS (ESI) m/z=273 [M+H]+. 1H NMR (400 MHz, d6-DMSO) δ 12.84 (s, 1H), 9.69 (s, 1H), 9.22 (d, J=2.0 Hz, 1H), 8.19 (dd, J=9.2 and 2.0 Hz, 1H), 7.77 (m, 1H), 7.54 (d, J=9.2 Hz, 1H), 7.37 (m, 2H), 6.69 (m, 1H)

المصدر