Sodium Hydroxide → 6-Chloroquinoline-3-carboxylic acid

HRID 489624Notes

Reaction equation

HRID 489624 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([O:14]CC)=[O:13])=[CH:5]2.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([OH:14])=[O:13])=[CH:5]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22265883Ethyl 6-chloroquinoline-3-carboxylate

Product 1

HCID 142414926-Chloroquinoline-3-carboxylic acidYield 82.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 6-chloroquinoline-3-carboxylate (0.19 g, 0.81 mmol) was saponified by treatment with dioxane (10 ml) and 10% aqueous sodium hydroxide (10 ml) at reflux for 3 hours. The dioxane was removed under vacuo; the aqueous solution remaining was acidified with HCl. The precipitated product was collected and washed with water to isolate 6-chloroquinoline-3-carboxylic acid as an off-white solid (0.14 g, 0.67 mmol). 1H NMR [(CD3OD), 300 MHz]: δ 9.35 (s, 1H), 8.95 (s, 1H), 8.17 (s, 1H), 8.1 (d, 2H), 7.87 (d, 1H).

Workup

  1. temperatureat reflux for 3 hours
  2. customThe dioxane was removed under vacuo
  3. customThe precipitated product was collected
  4. washwashed with water

Sources & evidence

ORD record
ord-838cad17652443188ec433fa80107fee
Source dataset
uspto-grants-2005_12
Patent number
US06977263B2

Reaction notes

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