4-Nitrophenol → 6-Methoxyquinoline

HRID 1890927Notes

Reaction equation

HRID 1890927 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[CH:10]1[C:15]([N+]([O-])=O)=CC=C(O)[CH:11]=1.S(=O)(=O)(O)O.[OH-].[Na+]>OCC(CO)O>[CH3:1][O:2][C:3]1[CH:9]=[C:8]2[C:6](=[CH:5][CH:4]=1)[N:7]=[CH:15][CH:10]=[CH:11]2

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 1118Sulfuric Acid2×HCID 7732P-AnisidineHCID 14798Sodium Hydroxide

Product 1

HCID 148606-MethoxyquinolineYield 83.8%

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of p-methoxyaniline (24.6 g, 0.2 mol), ferrous sulfate (8.34 g, 0.03 mol), glycerol (73.6 g, 60 mL), p-nitrophenol (16.68 g, 0.12 mol), and concentrated sulfuric acid (10 mL) was heated gently to 70° C. Then a second portion of concentrated sulfuric acid (25 mL) was added dropwise to the reaction mixture and it was stirred at reflux for 8 hours. After cooling down to room temperature, the reaction mixture was basified to pH=5.5 with 15% aqueous sodium hydroxide solution in an ice bath. The resulting precipitate was filtered, dried and 16 g of 6-methoxy-quinoline was obtained as a yellow solid (50% yield).

Workup

  1. temperatureat reflux for 8 hours
  2. temperatureAfter cooling down to room temperature
  3. filtrationThe resulting precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-14c1fe31986e4015bc8cb793337978cb
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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