6-Chloro-3-pyridinecarbonitrile → 6-(Octyloxy)pyridine-3-carbonitrile

HRID 128814

반응식

HRID 128814 반응식
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1.[CH2:10]([O-:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[Na+]>O>[CH2:10]([O:18][C:2]1[N:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][CH:3]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

참가 물질

4

반응물 2

HCID 51520946-Chloro-3-pyridinecarbonitrileHCID 23689331Sodium octylate

생성물 1

HCID 193751576-(Octyloxy)pyridine-3-carbonitrile수율 87.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 6-chloropyridine-3-carboxamide (14 g), phosphorous oxychloride (35 ml) and chloroform (120 ml) is refluxed for 2 hr, cooled, and concentrated. The residue is stirred with water and the resulting precipitate is collected and recrystallized from ethanol to provide 10.3 g (83 %) of 6-chloropyridine-3-carbonitrile. This nitrile (2.77 g) is added to a solution of sodium octanolate (prepared from 1-octanol (2.78 g) and sodium hydride (0.88g of 60% dispersion) in DMF (20 ml)). After 30 min at room temperature, the mixture is poured into water, and the product extracted with ether. The extracts are concentrated and chromatographed with 2:3 hexane-dichloromethane, to provide 6-(octyloxy)pyridine-3-carbonitrile as a colorless oil (3.7 g, 80%). This nitrile is dissolved in toluene (15 ml), cooled to -20°, and diisobutylaluminum hydride (12.5 ml of 1.5M solution in toluene) is added dropwise. After an hour, the mixture is poured into 1.0N hydrochloric acid and the product extracted with ether. The extracts are dried, filtered, and concentrated to leave 6-(octyloxy)pyridine-3-carboxaldehyde (2.36 g) as a yellow oil.

후처리

  1. extractionthe product extracted with ether
  2. concentrationThe extracts are concentrated
  3. customchromatographed with 2:3 hexane-dichloromethane

출처 및 근거

ORD 기록
ord-25312700d82443b4a619336fff79f3f9
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464865

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