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

HRID 2195534

反応式

HRID 2195534 の反応式
[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]

参加物

4

反応物 3

HCID 7764Ethyl cyanoacetateHCID 8028Tetrahydrofuran2 回HCID 5355751(3Z)-4-Amino-3-penten-2-one

生成物 1

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

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-bd55881dac5046d0ab7131fcbf7111b7
出典データセット
uspto-grants-2012_12
特許番号
USRE043878E1

関連ノート

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