Sodium Hydroxide → 1-Phenyl-1H-pyrazole-3-carboxylic acid

HRID 1178119ノート

反応式

HRID 1178119 の反応式
[O-:1][Mn](=O)(=O)=O.[K+].[CH3:7][C:8]1[CH:12]=[CH:11][N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:9]=1.[OH-:19].[Na+]>O>[C:13]1([N:10]2[CH:11]=[CH:12][C:8]([C:7]([OH:1])=[O:19])=[N:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 707833-methyl-1-phenyl-1H-pyrazoleHCID 516875Potassium Permanganate

生成物 1

HCID 123708741-Phenyl-1H-pyrazole-3-carboxylic acid収率 44.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
85 °C

実験手順

KMnO4 (1.2 g, 7.6 mmol) was added portionwise to a stirred solution of 3-Methyl-1-phenyl-1H-pyrazole (100 mg, 0.63 mmol) and NaOH (504 mg, 12.6 mmol) in H2O (4 mL). The resulting mixture was heated to 85° C. for 48 hrs. The reaction mixture was filtered, filtrate was acidified with 30% aqueous HCl solution, extracted the aqueous layer with EtOAc. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by washing with hexane to afford 53 mg (44.53% yield) of 1-phenyl-1H-pyrazole-3-carboxylic acid. 1H NMR (DMSO-d6): δ 8.6 (d, 1H), 7.9 (d, 2H), 7.6-7.5 (t, 2H), 7.4 (t, 1H), 6.96 (d, 1H).

後処理

  1. filtrationThe reaction mixture was filtered
  2. extractionextracted the aqueous layer with EtOAc
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. customThe obtained residue was purified
  7. washby washing with hexane

出典と根拠

ORDレコード
ord-ba1ce0e2994b4c648b7210d449061c20
出典データセット
uspto-grants-2010_11
特許番号
US07842696B2

反応ノート

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