Sodium Hydroxide → 3-Nitroquinolin-6-ol

HRID 1512112

반응식

HRID 1512112 반응식
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6]2.[OH-].[Na+]>Br>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6]2

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 15193946-Methoxy-3-nitroquinoline

생성물 1

HCID 595075803-Nitroquinolin-6-ol수율 78.3%

시약·촉매·용매 1

HCID 260Hydrogen Bromide용매

반응 조건

온도
120 °C

실험 절차

6-Methoxy-3-nitroquinoline (Magnus, P. et al., J. Am. Chem. Soc. 119, 5591, 1997; 100 mg, 0.49 mmol) was dissolved in hydrogen bromide solution (47% aq, 2.5 mL, 0.2 M), heated and stirred at 120° C. for 16 hours. The reaction mixture was cooled to room temperature, neutralized with 6N NaOH, then extracted with EtOAc (150 mL). The organic layer was dried over Na2SO4 and purified by flash chromatography (SiO2, 40-50% EtOAc/hexanes), obtaining 73 mg (78%) of 6-hydroxy-3-nitroquinoline. LC/MS (m/z): 190.9 (MH+), Rt 1.97 minutes.

후처리

  1. temperatureheated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with EtOAc (150 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. custompurified by flash chromatography (SiO2, 40-50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-2a1cb6516432495282e87d86b7de9836
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217035B2

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