Ethyl 7-methoxyquinoline-3-carboxylate → HCID 135819170, compound

HRID 322330Notes

Reaction equation

HRID 322330 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[N:10]2)=[CH:5][CH:4]=1>Br>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 21865246Ethyl 7-methoxyquinoline-3-carboxylate

Product 1

HCID 135819170HCID 135819170, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of ethyl 7-methoxy-3-quinolinecarboxylate (12.0 g) and 47% HBr (200 ml) was refluxed for 24 h. The precipitated crystals (12.63 g) were collected and added to a mixture of ethanol (400 ml) and conc.H2SO4 (2 ml). After refluxing for 20 h, the reaction mixture was concentrated, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated to give ethyl 7-hydroxy-3-quinoline-carboxylate (5.70 g, 51%). Recrystallization from ethyl acetate-hexane gave colorless prisms, 179-180° C.

Workup

  1. temperaturewas refluxed for 24 h
  2. customThe precipitated crystals (12.63 g) were collected
  3. additionadded to a mixture of ethanol (400 ml)
  4. temperatureAfter refluxing for 20 h
  5. concentrationthe reaction mixture was concentrated
  6. additiondiluted with saturated aqueous sodium bicarbonate
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with water
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-59359cc8b15d49fb96003ac6eea2b994
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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