Pyridine → 2-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-5-cyanopyridine

HRID 1870760ノート

反応式

HRID 1870760 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([NH2:19])=O)=[CH:13][N:12]=1)[CH2:9][CH3:10].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]#[N:19])=[CH:13][N:12]=1)[CH2:9][CH3:10]

参加物

5

反応物 3

HCID 1049Pyridine2 回HCID 9845Trifluoroacetic anhydride2 回HCID 183577602-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxamide

生成物 1

HCID 183577802-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-5-cyanopyridine収率 105.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxamide (example 4) (1.0 g, 2.85 mmol) was suspended in tetrahydrofuran (15 ml) and the stirred solution treated with pyridine (0.46 ml, 0.46 g, 5.7 mmol) and trifluoroacetic anhydride (0.9 ml, 1.35 g, 6.4 mmol) at ambient temperature (slight exotherm). A yellow colour became apparent and the solid dissolved in the THF. The solution was left standing at ambient temperature overnight, then further pyridine (0.46 ml, 5.7 mmol) and TFAA (0.90 ml, 6.4 mmol) were added and the reaction was again left overnight. The mixture was evaporated to low volume, saturated sodium bicarbonate solution was added and the mixture stirred at ambient temperature for 30 minutes, evaporated to low volume and the resultant white precipitate filtered, washed with water and air dried to give 2-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-5-cyanopyridine as a white solid (1.0 g, 100%).

後処理

  1. waitThe solution was left
  2. waitthe reaction was again left overnight
  3. customThe mixture was evaporated to low volume, saturated sodium bicarbonate solution
  4. additionwas added
  5. customevaporated to low volume
  6. filtrationthe resultant white precipitate filtered
  7. washwashed with water and air
  8. customdried

出典と根拠

ORDレコード
ord-067c319844a24c209c6e05793cc8e483
出典データセット
uspto-grants-2000_08
特許番号
US06100258

反応ノート

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