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

HRID 593870

반응식

HRID 593870 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
85 °C

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-952798e87ea34fe590227fa907cd7ca1
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242962B2

연결된 노트

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