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

HRID 1178119노트

반응식

HRID 1178119 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 123708741-Phenyl-1H-pyrazole-3-carboxylic acid수율 44.7%

시약·촉매·용매 1

HCID 962Water용매

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온도
85 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ba1ce0e2994b4c648b7210d449061c20
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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