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

HRID 1754098Notes

Reaction equation

HRID 1754098 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 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, 1 H), 8.53 (d, J=8.8, 1 H), 8.22 (d, J=8.8, 1 H), 7.60 (s, 1 H).

Workup

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

Sources & evidence

ORD record
ord-0f666bea94f341e6864a1f27a9919b48
Source dataset
uspto-grants-2015_10
Patent number
US09169211B2

Reaction notes

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