反応 #410830

反応方程式

7-chloro-4-hydroxy-2-(4′-methylphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione

trifluoroacetic acid

sodium borohydride

→

title compound

収率 97.1%

7-Chloro-4-hydroxy-5,10-dihydro-2-(4′-methylphenyl)pyridazino[4,5-b]quinoline-1-one

収率 97.1%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他the cooling bath removed
2. 2
   温度to warm to room temperature
3. 3
   workup.STIRRINGThis was then stirred at room temperature for 3 hours after which the reaction
4. 4
   workup.ADDITIONwas diluted with cold water (65 mL)
5. 5
   workup.STIRRINGstirred for an additional 10 minutes
6. 6
   抽出After this time, the resulting white mixture was extracted with ethyl acetate (120 mL)
7. 7
   洗浄The organic phase was washed with water (25 mL), brine (25 mL)
8. 8
   乾燥dried over Na2SO4
9. 9
   その他evaporated to dryness
10. 10
    その他The resulting residue was triturated
11. 11
    ろ過filtered twice
12. 12
    温度from warm ethyl acetate/hexane (2:1, 15 mL) and ethyl acetate (6 mL)
13. 13
    その他After drying

実験手順

To a suspension of 7-chloro-4-hydroxy-2-(4′-methylphenyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione (495 mg, 1.4 mmol) in tetrahydrofuran (25 mL) was added trifluoroacetic acid (4.5 ml, 58 mmol). The mixture was cooled to 0° C. with an ice bath and sodium borohydride (290 mg, 7.7 mmol) was added. The resulting solution was stirred at 0° C. for 15 minutes, the cooling bath removed, and the reaction mixture was allowed to warm to room temperature. This was then stirred at room temperature for 3 hours after which the reaction was diluted with cold water (65 mL) and stirred for an additional 10 minutes. After this time, the resulting white mixture was extracted with ethyl acetate (120 mL). The organic phase was washed with water (25 mL), brine (25 mL), dried over Na2SO4 and evaporated to dryness. The resulting residue was triturated and filtered twice from warm ethyl acetate/hexane (2:1, 15 mL) and ethyl acetate (6 mL). After drying, this afforded the title compound as a white solid (462 mg, 97%). MP=208-210° C. (d) MS(CI)340(m/e+1) NMR(d6-DMSO): 2.33(s,3H),3.79(s,2H), 6.92(dd,1H,J1=8.1Hz,J2=1.9Hz), 7.11(d,1H,J=8.2 Hz),7.24(app d, 3H), 7.43(d,2H,J=8.2Hz), 9.05(s,1H),11.99(s, 1H);

出典