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

HRID 1353656

反応式

HRID 1353656 の反応式
[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

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 6174445-Nitro-3-phenyl-1H-indazoleHCID 178418361HCID 178418361、化合物

生成物 1

HCID 224798623-phenyl-1H-indazole-5-ol収率 28%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 178418390HCID 178418390、化合物触媒

反応条件

温度
180 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-79aee9b4e9d344bc91c91eed0c74f744
出典データセット
uspto-grants-2007_05
特許番号
US07220771B2

関連ノート

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