反応式
N#N.[CH3:3][C:4]1([CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[N:14]2)[O:8][CH2:7][CH2:6][O:5]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][C:4]1([CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[C:16]([NH2:18])[CH:15]=[N:14]2)[O:8][CH2:7][CH2:6][O:5]1参加物
反応条件
- 温度
- 75 °C
実験手順
In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 1-[4-(2-methyl-[1,3]dioxolan-2-yl)-butyl]-4-nitro-1H-pyrazole (1.80 g, 7.05 mmol), iron powder (1.20 g, 21.26 mmol) and NH4Cl (1.90 g, 35.25 mmol) in a mixture of EtOH (46.0 mL) and water (23.0 mL) was stirred at 75° C. for 30 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (400 mL) was added followed by 1M NaOH (100 mL). The aq. layer was extracted with CH2Cl2 (2×100 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a deep red oil. LC-MS-conditions 02: tR=0.56 min; [M+H]+=226.53. 1H NMR (400 MHz, CDCl3) δ 1.29 (s, 3H), 1.34-1.46 (m, 2H), 1.61-1.70 (m, 2H), 1.77-1.88 (m, 2H), 2.85 (s, 2H), 3.86-3.92 (m, 2H), 3.92-3.96 (m, 2H), 3.99 (t, J=7.3 Hz, 2H), 7.00 (s, 1H), 7.14 (s, 1H).
後処理
- filtrationThe reaction mixture was filtered while hot and
- concentrationconcentrated under reduced pressure
- additionCH2Cl2 (400 mL) was added
- extractionThe aq. layer was extracted with CH2Cl2 (2×100 mL)
- dry with materialextracts were dried over MgSO4
- filtrationfiltered
- customthe solvents were removed under reduced pressure
出典と根拠
- ORDレコード
- ord-4ed3b585752540d2a300de4de9863fb5
- 出典データセット
- uspto-grants-2012_10
- 特許番号
- US08288419B2
関連ノート
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