반응 #332042

반응 방정식

Phosphorous oxychloride

6-bromo-3-nitroquinolin-4-ol

triethylamine

1-amino-2-methylpropan-2-ol

→

1-[(6-bromo-3-nitroquinolin-4-yl)amino]-2-methylpropan-2-ol

수율 90.8%

용매

water

N,N-dimethylformamide

tetrahydrofuran

반응 조건

후처리

1. 1
   온도cooled to ambient temperature
2. 2
   여과The resulting precipitate was filtered
3. 3
   세척washed with water
4. 4
   기타dried
5. 5
   기타The recovered solid was transferred to a round bottomed flask
6. 6
   workup.ADDITIONtetrahydrofuran (100 mL) was added
7. 7
   workup.STIRRINGThe reaction was stirred for 16 hours
8. 8
   workup.STIRRINGstirred for 15 minutes
9. 9
   여과The resulting yellow solid was filtered
10. 10
    기타dried

실험 절차

Phosphorous oxychloride (5.45 mL, 58.5 mmol) was added to a slurry of 6-bromo-3-nitroquinolin-4-ol (15 g, 55.7 mmol) in N,N-dimethylformamide (100 mL). The reaction mixture was heated to 100° C. for 10 minutes and then cooled to ambient temperature. The solution was poured into ice water (400 mL) and stirred for 20 minutes. The resulting precipitate was filtered, washed with water, and dried. The recovered solid was transferred to a round bottomed flask and tetrahydrofuran (100 mL) was added. A solution of triethylamine (11.6 mL, 83.5 mmol) and 1-amino-2-methylpropan-2-ol (5.21 g, 58.5 mmol) in tetrahydrofuran (20 mL) was added dropwise. The reaction was stirred for 16 hours. The mixture was poured into water and stirred for 15 minutes. The resulting yellow solid was filtered and dried to provide 17.2 g of 1-[(6-bromo-3-nitroquinolin-4-yl)amino]-2-methylpropan-2-ol as a yellow solid.

출처