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

HRID 62367

반응식

HRID 62367 반응식
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]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 977Oxygen2회HCID 7898CyanoacetamideHCID 12990Hexen-2-alHCID 23665647Potassium tert-butoxide2회

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5d9e9705125c4bf086a84d72e1ef96d7
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446041B2

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