Sodium Hydroxide → 2-Tert-butylquinoline-6-carboxylic acid

HRID 1094650

Reaction equation

HRID 1094650 reaction equation
[C:1]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([O:17]C)=[O:16])[CH:11]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.C1COCC1>[C:1]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([OH:17])=[O:16])[CH:11]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57458162Methyl 2-tert-butylquinoline-6-carboxylate

Product 1

HCID 207094322-Tert-butylquinoline-6-carboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-tert-butylquinoline-6-carboxylate (347 mg, 1.43 mmol) in MeOH (4 ml) and THF (4 ml) was added 2M aqueous sodium hydroxide (2 ml) at room temperature. The mixture was stirred at room temperature for 1.5 hours. Then evaporated, diluted with water (5 ml), neutralized to pH 5˜6 by 2M aqueous hydrochloride. The formed precipitate was collected, washed with water to furnish the title compound (282 mg, 86% yield) as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm 1.49 (9H, s),7.62 (1H, d, J=8.8 Hz), 8.13 (1H, d, J=8.8 Hz), 8.20 (1H, d, J=8.8 Hz), 8.31-8.34 (1H, m),8.64-8.66 (1H, m) MS (ESI): m/z 230 (M+H)+.

Workup

  1. customThen evaporated
  2. additiondiluted with water (5 ml)
  3. customThe formed precipitate was collected
  4. washwashed with water

Sources & evidence

ORD record
ord-258071e2c0ca4008b4dd056b31d80531
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Linked notes

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