Hydrogen Bromide → 6-Hydroxyquinoline-3-carboxylic acid

HRID 1894965Notes

Reaction equation

HRID 1894965 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]([OH:15])=[O:14])=[CH:6]2.Br>C(O)(=O)C>[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

4

Reactant 2

HCID 260Hydrogen BromideHCID 142415026-Methoxyquinoline-3-carboxylic acid

Product 1

HCID 589024556-Hydroxyquinoline-3-carboxylic acidYield 97.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

6-Methoxyquinoline-3-carboxylic acid (0.75 g, 3.69 mmol) was placed in a 20 mL microwave vial fitted with a stirbar. The solid was suspended in acetic acid (7 mL) and hydrobromic acid (48% in water, 3.5 mL) was added. The vial was capped and the suspension was carefully heated under microwave irradiation at 140° C. for 1 h. After reaction, the vial was thoroughly cooled to room temperature and very carefully vented with an 18 g needle in a fume hood prior to opening. The solids were collected by filtration and washed with ethyl acetate to afford the title product as a solid (0.678 g, 91%). LC-MS: (FA) ES+ 190; 1H NMR (400 MHz, d6-DMSO) δ ppm 10.68 (br s, 1H), 9.26 (d, J=1.9 Hz, 1H), 9.14 (d, J=1.3 Hz, 1H), 8.08 (d, J=9.1 Hz, 1H), 7.62 (dd, J=9.1, 2.7 Hz, 1H), 7.52 (d, J=2.7 Hz, 1H).

Workup

  1. customvial fitted with a stirbar
  2. customThe vial was capped
  3. customAfter reaction
  4. temperaturethe vial was thoroughly cooled to room temperature
  5. filtrationThe solids were collected by filtration
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-f0df10c2a28148aeaec8713b12c30adf
Source dataset
uspto-grants-2013_08
Patent number
US08513421B2

Reaction notes

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