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

HRID 872236Notes

Reaction equation

HRID 872236 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, 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-a3d238a4b42744468040ff7c0cb2a6a4
Source dataset
uspto-grants-2015_03
Patent number
US08975278B2

Reaction notes

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