Hydrochloric Acid → 1-(4-Fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 2095783노트

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HRID 2095783 반응식
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=[O:5])#[N:2].CO[CH:16]=[CH:17][C:18](=O)[CH3:19].N12CCN(CC1)CC2.CO/C=C/C(=O)C.Cl>COCCOCCO>[F:13][C:10]1[CH:9]=[CH:8][C:7]([N:6]2[C:18]([CH3:19])=[CH:17][CH:16]=[C:3]([C:1]#[N:2])[C:4]2=[O:5])=[CH:12][CH:11]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 9237Dabco2회HCID 942973-Buten-2-one, 4-methoxy-HCID 639675(3E)-4-Methoxy-3-buten-2-oneHCID 6931482-Cyano-N-(4-fluorophenyl)acetamide

생성물 1

HCID 669689251-(4-Fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile수율 31.2%

시약·촉매·용매 1

HCID 8134Diethylene Glycol Monomethyl Ether용매

반응 조건

온도
120 °C

실험 절차

A solution of 2-cyano-N-(4-fluorophenyl)acetamide (15 g, 84.2 mmol), 4-methoxybut-3-en-2-one (12.6 g, 125.9 mmol) and 1,4-diazabicyclo[2.2.2]octane (9.4 g, 84.2 mmol) in 2-(2-methoxyethoxy)ethanol (150 mL) was stirred with heating at 120° C. for 5 hr. (3E)-4-Methoxybut-3-en-2-one (4.2 g, 41.9 mmol) and 1,4-diazabicyclo[2,2,2]octane (4.7 g, 41.9 mmol) were further added to the reaction mixture, and the mixture was stirred with heating at 120° C. for 1 hr. 2N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained solid was washed with ethyl acetate to give the title compound (6 g, 31%) as a pale-brown solid.

후처리

  1. temperaturewith heating at 120° C. for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. washThe obtained solid was washed with ethyl acetate

출처 및 근거

ORD 기록
ord-6abd68b8f551418a9767a5734fd8a080
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445509B2

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