Hydrochloric Acid → 4-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 873419

反応式

HRID 873419 の反応式
CC([O-])(C)C.[K+].[C:7]([CH2:9][C:10]([NH2:12])=[O:11])#[N:8].[CH3:13][C:14](=O)[CH:15]=[CH:16][CH2:17][CH3:18].O=O.Cl>CS(C)=O.O>[CH2:17]([C:16]1[CH:15]=[C:14]([CH3:13])[NH:12][C:10](=[O:11])[C:9]=1[C:7]#[N:8])[CH3:18]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 977Oxygen2 回HCID 7898CyanoacetamideHCID 12990Hexen-2-alHCID 23665647Potassium tert-butoxide2 回

生成物 1

HCID 156418004-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile収率 31.7%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

To a stirred solution of t-BuOK (22.85 g, 204.08 mmol) and cyanoacetamide (18.8 g, 224.1 mmol) in DMSO (300 mL) was added hex-3-en-2-one (20 g, 204.08 mmol) under argon atmosphere at room temperature. The reaction mixture was then stirred at room temperature for 30 min and then added additional t-BuOK (68.5 g, 612.05 mmol) was added. Argon gas was displaced by oxygen gas and the mixture stirred for 48 hrs at room temperature in presence of oxygen. Reaction was monitored by TLC. The reaction mixture was cooled to 0° C. and diluted with water (100 mL) followed by 4 N HCl (120 mL). The mixture was stirred for 15 min and the resulting solid was filtered. The solid was washed with water (1 L) and dried to afford the title compound, 4-ethyl-1,2-dihydro-6-methyl-2-oxopyridine-3-carbonitrile (10.5 g, 31%), as an off white solid. 1H NMR (CDCl3, 400 MHz): δ ppm 1.148-1.185 (t, 3H, J=7.4 Hz), 2.237 (s, 3H), 2.557-2.614 (m, 2H), 6.211 (s, 1H), 12.330 (broad s, 1H). MS(ES) [M+H]+ 161.06.

後処理

  1. additionwas added
  2. customReaction
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. stirringThe mixture was stirred for 15 min
  5. filtrationthe resulting solid was filtered
  6. washThe solid was washed with water (1 L)
  7. customdried

出典と根拠

ORDレコード
ord-32e46b0dbd8f40ec885eabc553abf356
出典データセット
uspto-grants-2015_03
特許番号
US08975291B2

関連ノート

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