Water → 6-Bromoquinoline-2-carboxylic acid

HRID 2423385Notes

Reaction equation

HRID 2423385 reaction equation
S(=O)(=O)(O)[OH:2].[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:17](Br)(Br)Br)[CH:11]=[CH:10]2.[OH2:21]>>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:17]([OH:2])=[O:21])[CH:11]=[CH:10]2

Participants

4

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 593215826-Bromo-2-(tribromomethyl)quinoline

Product 1

HCID 123862086-Bromoquinoline-2-carboxylic acid

Conditions

Temperature
150 °C

Procedure

Concentrated sulfuric acid (0.75 L) was added during 15 min to a stirred suspension of 6-bromo-2-(tribromomethyl)quinoline (350 g, 0.76 mol) in water (1.75 L). The resulting suspension was heated at 150° C. (bath temperature) for 5 hr. The mixture was cooled and the precipitate was collected by filtration, washed with water and dried to give 6-bromo-2-quinolinecarboxylic acid as a solid (127.6 g). The filtrate was diluted with water (3 L) and a second crop of the product was obtained (55.7 g, combined yield 183.3 g, 96%). 1H NMR (400 MHz, DMSO-d6): 8.50 (d, J=9 Hz, 1H), 8.38 (d, J=2 Hz, 1H), 8.13 (d, J=9 Hz, 1H), 8.06 (d, J=9 Hz, 1H), 7.96 (m, 1H). ES-LCMS m/z 253 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-e1d0e4a8a22e4c8da38254fd22d08c33
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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