Lithium Hydroxide → 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazole-5-carboxylic acid

HRID 2042092Notes

Reaction equation

HRID 2042092 reaction equation
[OH-].[Li+].[C:3]([C:7]1[CH:11]=[C:10]([C:12]([O:14]CC)=[O:13])[N:9]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]3)[N:8]=1)([CH3:6])([CH3:5])[CH3:4]>O1CCOCC1.O.CCO>[C:3]([C:7]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[N:9]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[N:23]=[CH:22][CH:21]=[CH:20]3)[N:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67251871ethyl 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazole-5-carboxylate

Product 1

HCID 672531053-tert-butyl-1-(quinolin-6-yl)-1H-pyrazole-5-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 69104347Dioxane ethanol waterSolvent

Procedure

Lithium hydroxide (62 mg, 2.6 mmol) was added to a solution of ethyl 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazole-5-carboxylate (0.21 g, 0.65 mmol) in dioxane-H2O-EtOH (1:1:1, 6 mL). The reaction mixture was stirred overnight at RT. The solution was concentrated and the residue was dissolved in H2O (2 mL). 3M HCl was added and the precipitate was collected by filtration and washed with water. The solid was dried under vacuum to obtain 3-tert-butyl-1-(quinolin-6-yl)-1H-pyrazole-5-carboxylic acid (0.18 g, 94% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.96 (dd, J=2.0, 4.0 Hz, 1H), 8.47 (dd, J=1.2, 8.4 Hz, 1H), 8.09 (m, 1H), 8.06 (s, 1H), 7.82 (dd, J=2.8, 9.2 Hz, 1H), 7.61 (dd, J=4.8, 8.8 Hz, 1H), 7.01 (s, 1H), 1.33 (s, 9H); MS (ESI) m/z: 296.0 (M+H+).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue was dissolved in H2O (2 mL)
  3. addition3M HCl was added
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water
  6. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-62f2d7b6929e415fb621f54f7a13ca0f
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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