反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].[C:13]([O-:16])(=O)[CH3:14].[K+].C(OC(=O)C)(=O)C.C1OCCOCCOCCOCCOCCOC1.CCCCCO[N:49]=O>C(Cl)(Cl)Cl>[C:13]([N:12]1[C:11]2[C:2](=[CH:3][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:9][CH:10]=2)[CH:1]=[N:49]1)(=[O:16])[CH3:14]参加物
実験手順
To a stirred mixture of methyl 3-methyl-4-aminobenzoate (5.0 g, 30.0 mmol) and potassium acetate (2.94 g, 30.0 mmol) in chloroform (50 mL) is added acetic anhydride (5.66 mL, 60.0 mmol). The mixture is stirred for 30 min at rt, followed by the addition of 18-crown-6 (1.58 g, 6.0 mmol) and n-amyl nitrite (7.78 g, 66.0 mmol). The mixture is heated to reflux for 16 h, followed by cooling to rt. The mixture is washed sequentially with aqueous sodium bicarbonate solution (2×), water and brine. The organic layer is dried over MgSO4, filtered and concentrated in vacuo. The crude product is purified by flash chromatography on silica gel. Elution with hexanes-EtOAc (80:20) gives 3.1 g (47%) of methyl 1-acetyl-1H-indazole-5-carboxylate as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.52-8.50, 8.3, 8.2, 4.0, 2.8.
後処理
- temperatureThe mixture is heated
- temperatureto reflux for 16 h
- temperatureby cooling to rt
- washThe mixture is washed sequentially with aqueous sodium bicarbonate solution (2×), water and brine
- dry with materialThe organic layer is dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product is purified by flash chromatography on silica gel
- washElution with hexanes-EtOAc (80:20)
出典と根拠
- ORDレコード
- ord-6062662749034ec397236ef61309513e
- 出典データセット
- uspto-grants-2005_02
- 特許番号
- US06849620B2
関連ノート
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