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

HRID 1436961Notes

Reaction equation

HRID 1436961 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, 1 H), 8.22 (d, J=8.8, 1 H), 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-c633cdfa20ef4779b6fcadd137e9e156
Source dataset
uspto-grants-2009_11
Patent number
US07619091B2

Reaction notes

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