Acetic Acid → 6-Methylquinoline-2-carboxylic acid

HRID 1462916Notes

Reaction equation

HRID 1462916 reaction equation
C([N:9]1[C:18]2[C:13](=[CH:14][C:15]([CH3:19])=[CH:16][CH:17]=2)[CH:12]=[CH:11]C1C#N)(=O)C1C=CC=CC=1.Br.[C:23]([OH:26])(=[O:25])[CH3:24]>>[CH3:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:9]=[C:24]([C:23]([OH:26])=[O:25])[CH:11]=[CH:12]2

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 260Hydrogen BromideHCID 4672308HCID 4672308, compound

Product 1

HCID 123952026-Methylquinoline-2-carboxylic acid

Procedure

The resulting (±) 1-benzoyl-2-cyano-1,2-dihydro-6-methylquinoline thus obtained (155.2 g) was added to acetic acid (170 ml) and 48% hydrobromic acid (170 ml) and this mixture was stirred and refluxed for 0.5 hours. After cooling to room temperature, the solid was collected by filtration and then stirred in water (1000 ml) at 80°-90° while concentrated ammonium hydroxide was added until a pH of 8-9 was obtained. After cooling to 50°, acetic acid was added until a pH of 4-5 was reached. The 6-methyl-2-quinolinecarboxylic acid was collected by filtration and then recrystallized from acetic acid; yield 87 g, m.p. 208° (dec).

Workup

  1. temperaturerefluxed for 0.5 hours
  2. filtrationthe solid was collected by filtration
  3. stirringstirred in water (1000 ml) at 80°-90° while concentrated ammonium hydroxide
  4. additionwas added until a pH of 8-9
  5. customwas obtained
  6. temperatureAfter cooling to 50°
  7. filtrationThe 6-methyl-2-quinolinecarboxylic acid was collected by filtration
  8. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-4252ec1b4c594496b9b4f26790a57a39
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

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