Sodium hydride → 4-(5-Methyl-3-nitropyrid-2-yl)-4,4-bis(carbethoxy)butyronitrile

HRID 326080

반응식

HRID 326080 반응식
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH2:11][CH2:12][C:13]#[N:14])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H-].[Na+].Cl[C:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][C:22]([CH3:28])=[CH:21][N:20]=1>O1CCCC1>[CH3:28][C:22]1[CH:23]=[C:24]([N+:25]([O-:27])=[O:26])[C:19]([C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:15])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:11][CH2:12][C:13]#[N:14])=[N:20][CH:21]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 87005Diethyl (2-cyanoethyl)malonateHCID 8183002-Chloro-5-methyl-3-nitropyridine

생성물 1

HCID 202714614-(5-Methyl-3-nitropyrid-2-yl)-4,4-bis(carbethoxy)butyronitrile수율 37.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

2-(2-Cyanoethyl)malonic acid diethylester (40 g) was reacted with sodium hydride (4.4 gm) in tetrahydrofuran at 20° C. 2-Chloro-5-methyl-3-nitro-pyridine (35 g) was added and the internal temperature was raised to 100° C. (some tetrahydrofuran distilled off) over 4.25 hrs. The reaction mixture was partitioned between chloroform and water and treated with charcoal. Vacuum distillation of the chloroform extract and then chromatography (CHCl3, silica column) of the distillation residues gave 4-(5-methyl-3-nitropyrid-2-yl)-4,4-bis (carbethoxy)-butyronitrile (24.5 g) as a yellow solid m.p. 48°-49° C.

후처리

  1. distillationdistilled off) over 4.25 hrs
  2. customThe reaction mixture was partitioned between chloroform and water
  3. additiontreated with charcoal
  4. distillationVacuum distillation of the chloroform
  5. extractionextract

출처 및 근거

ORD 기록
ord-882e8c6f2e234edd870a34a332a8835a
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04444772

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