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

HRID 1631017노트

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HRID 1631017 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 585542055-Chloro-6-(2-hydroxyethylamino)nicotinonitrile수율 89.3%

시약·촉매·용매 2

HCID 15413tert-Butyl methyl ether용매HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b11165d2daa7499a92542ae889486fb3
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791142B2

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