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

HRID 513923Notes

Reaction equation

HRID 513923 reaction equation
OC1C=C2C(C=C(C(O)=O)C=N2)=CC=1.C[O:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[C:22]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:23]=[N:24]2)=[CH:19][CH:18]=1>Br>[OH:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[C:22]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:23]=[N:24]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 21865246Ethyl 7-methoxyquinoline-3-carboxylateHCID 1361076117-Hydroxyquinoline-3-carboxylic acid

Product 1

HCID 135819170HCID 135819170, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
105 °C

Procedure

7-Hydroxyquinoline-3-carboxylic acid. Ethyl 7-methoxyquinoline-3-carboxylate (7.03 g, 30.4 mmol) was dissolved in HBr (48% aq., 150 mL) and was heated at 105° C. for 88.5 h. The reaction was cooled to ambient temperature and the precipitate was collected by filtration to afford the title compound as a brown solid (5.2 g, 90%). 1H NMR (400 MHz, DMSO-d6) δ 12.05-11.67 (m, 1H), 9.49 (d, J=2.0 Hz, 1H), 9.43 (s, 1H), 8.39 (d, J=9.8 Hz, 1H), 7.55-7.51 (m, 2H). [M+H]=190.2.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-a210e6c0484242c3bd8415ff4555baf4
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

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