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Triphenylphosphine → 4-(Aminomethyl)-3-chlorobenzonitrile
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | 4-Azidomethyl-3-chlorobenzonitrile | HCID 22349974 | — |
| 溶媒 | Oxolane--water (1/1) | HCID 21881883 | — |
| 生成物 | 4-(Aminomethyl)-3-chlorobenzonitrile | HCID 4089788 | 90% |
反応手順
To a solution of 2-choro-4-cyanobenzyl azide (5.8 g, 30.1 mmol) in THF/H2O (3:1), was added triphenyl phosphine (12.3 g, 46.7 mmol). The reaction was stirred at room temperature overnight, then neutralized with 1N sodium hydroxide, extracted with ethyl acetate (150 ml×3). The organic layer was dried over sodium sulfate, and then solvent was removed in vacuo. The product was purified by silica-gel chromatography column with methanol/ammonia hydroxide/ethyl acetate (20:1:69) to give 4.5 g (90%) of 2-chloro-4-cyanobenzylamine. NMR (CDCl3): δ 4.0 (s, 2H, CH2), 7.58 (d, 2H, HAr), 7.62 (s, 1H, HAr)
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06919347B2 |
| 出典データセット | uspto-grants-2005_07 |
| ORD ID | ord-e48da4a9ef5343e9957067963b6369f3 |
| 出典メモ | uspto-grants-2005_07 |