Ethyl cyanoacetate → Ethyl 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 2195534

반응식

HRID 2195534 반응식
[NH2:1]/[C:2](/[CH3:7])=[CH:3]\[C:4](=O)[CH3:5].[C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#N.C1C[O:19]CC1>>[CH3:5][C:4]1[CH:3]=[C:2]([CH3:7])[NH:1][C:8](=[O:19])[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

참가 물질

4

반응물 3

HCID 7764Ethyl cyanoacetateHCID 8028Tetrahydrofuran2회HCID 5355751(3Z)-4-Amino-3-penten-2-one

생성물 1

HCID 247443Ethyl 4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxylate수율 19.9%

실험 절차

A solution of (Z)-4-aminopent-3-en-2-one (20.0 g, 0.2 mol) in dry THF (20 mL) is added to a solution of ethyl cyanoacetate (22.6 g, 0.2 mol) and TEA (20.2 g, 0.2 mol) in dry THF (200 mL). The reaction mixture is heated at reflux for 56 hours and then concentrated. The residue is kept standing at RT for 5 hours and the precipitate is filtered and washed with EtOAc to afford the title compound (7.3 g, 19.9% yield). MS (m/z): 196.0 (M+H).

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 56 hours
  3. concentrationconcentrated
  4. filtrationthe precipitate is filtered
  5. washwashed with EtOAc

출처 및 근거

ORD 기록
ord-bd55881dac5046d0ab7131fcbf7111b7
출처 데이터셋
uspto-grants-2012_12
특허 번호
USRE043878E1

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