Sodium Hydroxide → 3-Nitroquinolin-6-ol

HRID 1512112Notes

Reaction equation

HRID 1512112 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-2a1cb6516432495282e87d86b7de9836
Source dataset
uspto-grants-2012_07
Patent number
US08217035B2

Reaction notes

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