Lithium Hydroxide → 2-Chloroquinoline-7-carboxylic acid

HRID 881001Notes

Reaction equation

HRID 881001 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12]([O:14]CC)=[O:13])=[CH:7][CH:8]=2)[N:3]=1.[OH-].[Li+]>O1CCCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12]([OH:14])=[O:13])=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 72942632Ethyl 2-chloroquinoline-7-carboxylate

Product 1

HCID 337786142-Chloroquinoline-7-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-chloroquinoline-7-carboxylate (800 mg, 3.4 mmol) in tetrahydrofuran (10 mL) was added 1 N aqueous lithium hydroxide (7 mL, 7 mmol). The reaction was stirred at room temperature overnight. The reaction was concentrated and the residue was diluted with water and acidified with 1 N aqueous hydrochloric acid. The resulting precipitate was collected by filtration and dried under vacuum to give the title compound (648 mg, 92%) as a white powder. +ESI (M+H) 208.1; 1H NMR (400 MHz, DMSO-d6, δ): 13.43 (s, 1H), 8.53 (d, J=8.7 Hz, 1H), 8.44-8.45 (m, 1H), 8.14 (d, J=8.4 Hz, 1H), 8.07-8.11 (m, 1H), 7.70 (d, J=8.5 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated
  2. additionthe residue was diluted with water
  3. filtrationThe resulting precipitate was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-37e6c51943cb4e2d9e15aa8fd46eb667
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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