Hydrochloric Acid → 5,7-Dichloro-8-hydroxyquinoline-2-carboxylic acid

HRID 623413Notes

Reaction equation

HRID 623413 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([O:13]CC2C=CC=CC=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:21]([OH:23])=[O:22])=[N:7]2.Cl>>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:21]([OH:23])=[O:22])=[N:7]2

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 57939368HCID 57939368, compound

Product 1

HCID 219181905,7-Dichloro-8-hydroxyquinoline-2-carboxylic acid

Procedure

A mixture of 5,7-dichloro-8-benzyloxy-quinoline-2-carboxylic acid 18 (2.56 g, 7.35 mmol) and concentrated hydrochloric acid (25 mL) was stirred at RT for 48 h, and then concentrated to dryness. The resulting residue was washed with diethyl ether (20 mL×2). This provided 5,7-dichloro-8-hydroxyquinoline-2-carboxylic acid 19 as a yellow solid (1.78 g, 94%). 1H NMR (CDCl3/DMSO-d6 (19:1), 400 MHz): δ 10.60 (br, 1H), 8.53 (d, J=8.8, 1H), 8.22 (d, J=8.8, 1H), 7.60 (s, 1H).

Workup

  1. concentrationconcentrated to dryness
  2. washThe resulting residue was washed with diethyl ether (20 mL×2)

Sources & evidence

ORD record
ord-3e521a65942d4adda5d0c10647cb41c6
Source dataset
uspto-grants-2016_04
Patent number
US09302993B2

Reaction notes

Loading…