Tetrahydrofuran → 2-Quinolinecarboxylic acid, 5-bromo-8-methoxy-

HRID 2393093Notes

Reaction equation

HRID 2393093 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:14]([O:16]C)=[O:15])=[N:7]2.O1CCCC1.O.[OH-].[Li+]>O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:14]([OH:16])=[O:15])=[N:7]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 9900802HCID 9900802, compound

Product 1

HCID 99436352-Quinolinecarboxylic acid, 5-bromo-8-methoxy-Yield 0.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 5-bromo-8-methoxyquinoline-2-carboxylate (154 g), tetrahydrofuran (40 ml), water (40 ml) and lithium hydroxide monohydrate (0.436 g) were combined and stirred at room temperature for 1.5 h. The tetrahydrofuran was removed in vacuo and the resulting aqueous mixture was acidified with hydrochloric acid. The resulting white precipitate was collected by filtration and dried in vacuo to give the title compound (1.33 g) as a white solid.

Workup

  1. customThe tetrahydrofuran was removed in vacuo
  2. filtrationThe resulting white precipitate was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-1c10f43d65074e3585a16ba9b4f4a23f
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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