Lithium Hydroxide → 2-Methoxy-7-quinolinecarboxylic acid

HRID 537149Notes

Reaction equation

HRID 537149 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([C:13]([O:15]CC)=[O:14])=[CH:8][CH:9]=2)[N:4]=1.[OH-].[Li+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][C:7]([C:13]([OH:15])=[O:14])=[CH:8][CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67491407Ethyl 2-methoxyquinoline-7-carboxylate

Product 1

HCID 674915922-Methoxy-7-quinolinecarboxylic acidYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-methoxyquinoline-7-carboxylate (125 mg, 0.54 mmol) in tetrahydrofuran (1.5 mL) was added 2 N aqueous lithium hydroxide (0.81 mL, 1.6 mmol). The reaction was stirred at room temperature for 65 hours. The tetrahydrofuran was removed in vacuo and the residue was acidified to pH=4 with 1 N aqueous hydrochloric acid. The mixture was diluted with water and the resulting precipitate was collected by filtration and dried under vacuum to give the title compound (106 mg, 96%) as a white solid. +ESI (M+H) 204.2; 1H NMR (400 MHz, CDCl3, δ): 8.64 (d, J=1.37 Hz, 1H), 8.01-8.04 (m, 1H), 8.01 (s, 1H), 7.79 (d, J=8.58 Hz, 1H), 7.01 (d, J=8.78 Hz, 1H), 4.09 (s, 3H).

Workup

  1. customThe tetrahydrofuran was removed in vacuo
  2. additionThe mixture was diluted with water
  3. filtrationthe resulting precipitate was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-dcfe978371cf4706a452ef610ca86b56
Source dataset
uspto-grants-2014_10
Patent number
US08859773B2

Reaction notes

Loading…