Ethyl 6-methoxyquinoline-3-carboxylate → 6-Hydroxyquinoline-3-carboxylic acid

HRID 1640118Notes

Reaction equation

HRID 1640118 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]([C:13]([O:15]CC)=[O:14])=[CH:6]2>Br>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]([OH:15])=[O:14])=[CH:6]2

Participants

3

Reactant 1

HCID 304668Ethyl 6-methoxyquinoline-3-carboxylate

Product 1

HCID 589024556-Hydroxyquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

Ethyl 6-methoxyquinoline-3-carboxylate (500 mg, 2.0 mmol) in 48% aq. HBr (5 mL) was subjected to MWI at 140° C. for 5 min. 6-Hydroxyquinoline-3-carboxylic acid precipitated from the reaction mixture and was collected by filtration. 1H NMR (300 MHz, CD3OD): δ 9.50 (d, 1H), 9.36 (d, 1H), 8.18 (d, 1H), 7.83 (dd, 1H), and 7.64 (d, 1H). LCMS: (FA) ES+ 190.1.

Workup

  1. custom6-Hydroxyquinoline-3-carboxylic acid precipitated from the reaction mixture
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-833447c5f1764bdf85a654f9a1c81fba
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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