Sodium Hydroxide → 3-Nitroquinolin-6-ol

HRID 1043783

反応式

HRID 1043783 の反応式
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

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 15193946-Methoxy-3-nitroquinoline

生成物 1

HCID 595075803-Nitroquinolin-6-ol収率 78.3%

試薬・触媒・溶媒 1

HCID 260Hydrogen Bromide溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b540758489894aadb3813cec2b442019
出典データセット
uspto-grants-2013_10
特許番号
US08563549B2

関連ノート

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