Lithium hydroxide, monohydrate → Quinoline-7-carboxylic acid

HRID 2235134Notes

Reaction equation

HRID 2235134 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[N:15]2)=[CH:10][CH:9]=1)=[O:7]>O.O1CCCC1>[N:15]1[C:16]2[C:11](=[CH:10][CH:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:17]=2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 12554532Methyl quinoline-7-carboxylate

Product 1

HCID 599475Quinoline-7-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide monohydrate (5.42 g, 141 mmol, 3 equiv.) in water (50 ml) was added to a solution of quinoline-7-carboxylic acid methyl ester (8.8 g, 47 mmol) in tetrahydrofuran (200 ml) and the solution was stirred at room temperature for 16 hours. The tetrahydrofuran was evaporated under reduced pressure and the solution adjusted to pH 7 with 1N HCl (aq) (141 ml), forming a white precipitate. The precipitate was filtered and washed with water and heptane. The solid was dried in a vacuum oven at 50° C. to give quinoline-7-carboxylic acid, 8.4 g (100% yield) as a white solid. LC @215 nm; Rt 0.66: 100%, m/z (ES+): 174 (M+H+.); δH (400 MHz; d6-DMSO) 9.02 (1H, dd), 8.58 (1H, s), 8.48 (1H, d), 8.09 (2H, m), 7.66 (1H, dd).

Workup

  1. customThe tetrahydrofuran was evaporated under reduced pressure
  2. customforming a white precipitate
  3. filtrationThe precipitate was filtered
  4. washwashed with water and heptane
  5. customThe solid was dried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-8948219f2f1c4543866ab3d97ba0b693
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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