Hydrochloric Acid → Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate

HRID 593870

反応式

HRID 593870 の反応式
C(O[C:4]([CH3:13])=[CH:5][C:6](=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])C.[C:14]([CH2:16][C:17]([NH2:19])=[O:18])#[N:15].C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[C:14]([C:16]1[C:17](=[O:18])[NH:19][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[CH3:13])#[N:15]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7898CyanoacetamideHCID 11430Potassium CarbonateHCID 275522CID 275522

生成物 1

HCID 275523Ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate収率 65.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
85 °C

実験手順

To a stirred solution of ethyl 4-ethoxy-2-oxopent-3-enoate (22.5 g, 121 mmol) and 2-cyanoacetamide (9.0 g, 107 mmol) in acetone (250 mL) was added potassium carbonate (15.8 g, 114 mmol). The reaction was refluxed (85° C. oil bath) for 10 hr (the reaction formed a thick ppt. in a deep red solution). The slurry was added to cold 1N HCl (230 mL) in ice. After stirring for 30 min. the suspension was filtered, washed with water and dried under vacuum to give the product ethyl 5-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-carboxylate (14.51 g, 70.4 mmol, 65.7% yield) as a light pink solid. 1H NMR (400 MHz, DMSO-d6) δ12.60 (br. s., 1H), 7.05 (br. s., 1H), 4.34 (q, J=7.1 Hz, 2H), 2.45 (s, 3H), 1.32 (t, J=7.1 Hz, 3H). MS(ES)+ m/e 206.8 [M+H]+.

後処理

  1. customformed a thick ppt
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried under vacuum

出典と根拠

ORDレコード
ord-952798e87ea34fe590227fa907cd7ca1
出典データセット
uspto-grants-2016_01
特許番号
US09242962B2

関連ノート

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