Ethyl Acetate → 3-phenyl-1H-indazole-5-ol

HRID 1272736

반응식

HRID 1272736 반응식
[N+]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O-])=O.[H][H].C(OCC)(=[O:23])C>[Pd].[Pd].[C]>[C:13]1([C:7]2[C:6]3[C:10](=[CH:11][CH:12]=[C:4]([OH:23])[CH:5]=3)[NH:9][N:8]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 6174445-Nitro-3-phenyl-1H-indazoleHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 224798623-phenyl-1H-indazole-5-ol수율 28%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 178418390HCID 178418390, 화합물촉매

반응 조건

온도
180 °C

실험 절차

To a solution of 5-nitro-3-phenyl-1H-indazole (1.0 g, 4.2 mmol) in ethyl acetate (80 mL) was added palladium on activated carbon (Pd/carbon) then the reaction was subjected to an atmosphere of hydrogen. The reaction was stirred for 3 days when the Pd/carbon was filtered off and the solution concentrated to an oil under vacuo. The oil was then taken up in H2SO4 (6 mL) and water (60 mL) and the suspension was heated in a bomb to 180° C. for 2 days. The reaction was then cooled to room temperature, quenched with NaHCO3 (100 mL) and extracted with ethyl acetate (3×30 mL). The organic layers were combined and dried (Na2SO4) and concentrated to recover the title compound (250 mg, 28% yield). 1H NMR (CDCl3) δ 13.0 (s, 1H), 9.20 (s, 1H), 7.91 (s, 1H), 7.88 (s, 1H), 7.50 (t, 2H), 7.41 (d, 1H), 7.36 (t, 1H), 7.28 (s, 1H), 6.96 (dd, 1H); ES-MS (m/z) 195 [M+1]+.

후처리

  1. filtrationwas filtered off
  2. concentrationthe solution concentrated to an oil under vacuo
  3. temperatureThe reaction was then cooled to room temperature
  4. customquenched with NaHCO3 (100 mL)
  5. extractionextracted with ethyl acetate (3×30 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-585974251c2b4a6ca14240322bb05e1c
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208513B2

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