Sodium Hydroxide → 3-Nitroquinolin-6-ol

HRID 1043783

Reaction equation

HRID 1043783 reaction equation
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

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15193946-Methoxy-3-nitroquinoline

Product 1

HCID 595075803-Nitroquinolin-6-olYield 78.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b540758489894aadb3813cec2b442019
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Linked notes

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