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

HRID 2042092ノート

反応式

HRID 2042092 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 69104347Dioxane ethanol water溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-62f2d7b6929e415fb621f54f7a13ca0f
出典データセット
uspto-grants-2013_11
特許番号
US08586565B2

反応ノート

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