Hydrochloric Acid → 6-Bromo-3-hydroxyquinoline-4-carboxylic acid

HRID 2307784Notes

Reaction equation

HRID 2307784 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=O)[C:5]2=[O:12].[OH-].[K+].BrC[C:17](=O)[C:18]([OH:20])=[O:19].Cl>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]=[CH:6][C:5]([OH:12])=[C:17]2[C:18]([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 68895-BromoisatinHCID 14797Potassium HydroxideHCID 70684Bromopyruvic Acid

Product 1

HCID 226072156-Bromo-3-hydroxyquinoline-4-carboxylic acidYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5-bromoisatin (2.26 g, 10 mmol) and potassium hydroxide (4.48 g, 80 mmol) in water (10 mL) was warmed until the materials were dissolved then cooled to room temperature, treated with bromopyruvic acid (2.3 g, 14 mmol), stirred for 6 days, adjusted to pH <7 with concentrated HCl, and filtered. The solid was washed with water and ethanol and dried to provide the desired product (1.5 g, 58%). MS (DCI/NH3) m/e 269 (M+H)+.

Workup

  1. dissolutionwere dissolved
  2. filtrationfiltered
  3. washThe solid was washed with water and ethanol
  4. customdried

Sources & evidence

ORD record
ord-3f7e934123bc4bbd848614d0d557abb7
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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