Ethanolamine → 5-Chloro-6-(2-hydroxyethylamino)nicotinonitrile

HRID 1631017ノート

反応式

HRID 1631017 の反応式
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:11]([CH2:13][NH2:14])[OH:12]>O1CCOCC1.CC(OC)(C)C>[Cl:1][C:2]1[C:3]([NH:14][CH2:13][CH2:11][OH:12])=[N:4][CH:5]=[C:6]([CH:9]=1)[C:7]#[N:8]

参加物

5

反応物 2

HCID 700EthanolamineHCID 128784645,6-Dichloropyridine-3-carbonitrile

生成物 1

HCID 585542055-Chloro-6-(2-hydroxyethylamino)nicotinonitrile収率 89.3%

試薬・触媒・溶媒 2

HCID 15413tert-Butyl methyl ether溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

A mixture of 5,6-dichloro-nicotinonitrile (Bionet GC-0755, 500 mg, 2.89 mmol) and ethanolamine (0.87 mL, 14.45 mmol) was prepared in anhydrous dioxane (5 mL) and heated at 80° C. for 24 hours. The reaction mixture was diluted with MTBE (50 mL) and washed with water (2×25 mL) and brine (25 ml). The aqueous layers were extracted with MTBE (50 mL). The organic layers were combined, dried (Na2SO4) and concentrated under reduced pressure to give the title compound as a white powder (510 mg, 89%). HPLC (Method A), Rt: 1.9 min (purity: 99.9%). UPLC/MS, M−(ESI): 196.0.

後処理

  1. washwashed with water (2×25 mL) and brine (25 ml)
  2. extractionThe aqueous layers were extracted with MTBE (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-b11165d2daa7499a92542ae889486fb3
出典データセット
uspto-grants-2014_07
特許番号
US08791142B2

反応ノート

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