반응 #1494345

반응 방정식

NaOH

5-methoxy-4-oxo-1-(2,2,6-trifluoro-1,3-benzodioxol-5-yl)-1,4-dihydropyridazine-3-carboxylic acid

DPPA

Et3N

→

title compound

수율 65.3%

3-Amino-5-methoxy-1-(2,2,6-trifluoro-1,3-benzodioxol-5-yl)pyridazin-4(1H)-one

수율 65.3%

용매

toluene

반응 조건

후처리

1. 1
   추출extracted with EtOAc
2. 2
   건조dried over Na2SO4
3. 3
   여과filtered
4. 4
   농축concentrated in vacuo
5. 5
   기타purified by column chromatography on basic silica gel (hexane/EtOAc=50/50 to 0/100)
6. 6
   기타recrystallized with EtOAc/hexane

실험 절차

A mixture of 5-methoxy-4-oxo-1-(2,2,6-trifluoro-1,3-benzodioxol-5-yl)-1,4-dihydropyridazine-3-carboxylic acid (1.18 g, 3.42 mmol), DPPA (1.10 mL, 5.13 mmol) and Et3N (0.715 mL, 5.13 mmol) in toluene (12 mL) was heated to 100° C. for 1 h. To the mixture was added 8 M NaOH aqueous solution (4.3 mL) at 0° C. The mixture was stirred at room temperature for 1 h, extracted with EtOAc, dried over Na2SO4, filtered, concentrated in vacuo and purified by column chromatography on basic silica gel (hexane/EtOAc=50/50 to 0/100) and recrystallized with EtOAc/hexane to yield the title compound (704 mg, 65% yield) as a white solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.73 (3H, s), 6.21 (2H, s), 7.85 (1H, d, J=9.4 Hz), 7.90 (1H, d, J=6.4 Hz), 8.33 (1H, s).

출처