6-Methoxy-8-nitroquinoline → 8-Nitroquinolin-6-ol

HRID 428542Notes

Reaction equation

HRID 428542 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[OH-].[Na+]>Br>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 68226-Methoxy-8-nitroquinolineHCID 14798Sodium Hydroxide

Product 1

HCID 2262598-Nitroquinolin-6-olYield 32.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent2×

Procedure

A solution of 6-methoxy-8-nitro-quinoline (9 g, 44.1 mmol) in HBr (100 mL) as heated at 110° C. overnight. Additional HBr (80 mL) was added and the reaction continued to heat for an additional 24 hours. The cooled reaction mixture was basified with 2.5 N NaOH (800 mL) and extracted into EtOAc (2×300 mL). The organic fractions were combined, dried over Na2SO4 and purified by column chromatography (50% EtOAc/hexane) to afford 2.71 g (32%) of the title compound as a white solid: mp discolors above 100° C., MS(−)ESI m/z 189 [M−H]−.

Workup

  1. temperatureto heat for an additional 24 hours
  2. customThe cooled reaction mixture
  3. extractionextracted into EtOAc (2×300 mL)
  4. dry with materialdried over Na2SO4
  5. custompurified by column chromatography (50% EtOAc/hexane)

Sources & evidence

ORD record
ord-d191a7160646414f81a0d9e8f9533240
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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