Hydrochloric Acid → 4-Methyl-5-hydroxy-6-methoxy-8-nitroquinoline

HRID 1388560Notes

Reaction equation

HRID 1388560 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([N+:16]([O-:18])=[O:17])[CH:8]=[C:9]([O:14][CH3:15])[C:10]=2[O:12]C)[N:5]=[CH:4][CH:3]=1.Cl>C(O)C>[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([N+:16]([O-:18])=[O:17])[CH:8]=[C:9]([O:14][CH3:15])[C:10]=2[OH:12])[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 6191084-Methyl-5,6-dimethoxy-8-nitroquinoline

Product 1

HCID 1357785114-Methyl-5-hydroxy-6-methoxy-8-nitroquinolineYield 92.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Methyl-5,6-dimethoxy-8-nitroquinoline (6.21 g, 25 mmol) was dissolved in ethanol (100 mL) containing concentrated hydrochloric acid (4.7 mL). The mixture was heated under reflux for 21 hours, then cooled to 10° and filtered. The solid was washed with cold (10°) ethanol (18 mL) followed by petroleum ether (15 mL) and air-dried to yield 5.41 g (92%) of the title compound, mp 253°-257° (dec).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 21 hours
  3. temperaturecooled to 10°
  4. filtrationfiltered
  5. washThe solid was washed with cold (10°) ethanol (18 mL)
  6. customair-dried

Sources & evidence

ORD record
ord-27f7fd6114bf4eb9b4351693909f46e8
Source dataset
uspto-grants-1984_02
Patent number
US04431807

Reaction notes

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