Cyanoacetamide → 4-Methyl-2-oxo-6-(phenylmethyl)-1,2-dihydro-3-pyridinecarbonitrile

HRID 62382

반응식

HRID 62382 반응식
[C:1]1([CH2:7][C:8](=O)[CH2:9][C:10](=O)[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]([CH2:16][C:17]([NH2:19])=[O:18])#[N:15].N1CCCCC1>CCO.O>[CH3:11][C:10]1[NH:19][C:17](=[O:18])[C:16]([C:14]#[N:15])=[C:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:9]=1.[CH3:11][C:10]1[CH:9]=[C:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:19][C:17](=[O:18])[C:16]=1[C:14]#[N:15]

참가 물질

7

반응물 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 187232,4-Pentanedione, 1-phenyl-

생성물 2

HCID 674668016-Methyl-2-oxo-4-(phenylmethyl)-1,2-dihydro-3-pyridinecarbonitrileHCID 674670424-Methyl-2-oxo-6-(phenylmethyl)-1,2-dihydro-3-pyridinecarbonitrile수율 103.4%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
75 °C

실험 절차

1-Phenyl-2,4-pentanedione (18.32 g, 104 mmol) and cyanoacetamide (8.74 g, 104 mmol) were dissolved in EtOH (104 mL) and heated until homogenous (ca. 75° C.). Piperidine (8.86 g, 104 mmol) was added and the reaction mixture heated at reflux for 15-30 min. followed by cooling to room temperature, during which time precipitation occurred. The heterogenous contents were filtered to give a solid which was suspended in 200 mL water and stirred vigorously for 20 min. The heterogenous mixture was filtered to afford 6-methyl-2-oxo-4-(phenylmethyl)-1,2-dihydro-3-pyridinecarbonitrile and 4-methyl-2-oxo-6-(phenylmethyl)-1,2-dihydro-3-pyridinecarbonitrile (12.06 g, 52%). LCMS MH+=225.1 1H NMR (400 MHz, DMSO-d6) (mixture of compounds) δ 7.21-7.31 (m, 10H), 6.06 (s, 2H), 3.89 (s, 2H), 3.79 (s, 2H), 2.24 (s, 3H), 2.15 (s, 3H).

후처리

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 15-30 min.
  3. temperatureby cooling to room temperature, during which time precipitation
  4. filtrationThe heterogenous contents were filtered
  5. customto give a solid which
  6. filtrationThe heterogenous mixture was filtered

출처 및 근거

ORD 기록
ord-23cff08d0f68473393e51e313b707bbf
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446041B2

연결된 노트

불러오는 중…