Selenium Dioxide → 2-(2,6-Dichloro-phenylamino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinoline-7-carbaldehyde

HRID 562425노트

반응식

HRID 562425 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[N:11]([CH3:26])[C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH3:23])=[C:17]([CH3:24])[C:16]=3[CH:15]=[CH:14][C:13]=2[N:25]=1.[Se](=O)=[O:28]>O1CCOCC1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][C:10]1[N:11]([CH3:26])[C:12]2[C:21]3[C:20](=[O:22])[NH:19][C:18]([CH:23]=[O:28])=[C:17]([CH3:24])[C:16]=3[CH:15]=[CH:14][C:13]=2[N:25]=1

참가 물질

4

반응물 2

HCID 24007Selenium DioxideHCID 99082472-(2,6-Dichloro-phenylamino)-1,6,7-trimethyl-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one

생성물 1

HCID 108622852-(2,6-Dichloro-phenylamino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinoline-7-carbaldehyde수율 72.4%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

To a 200 mL round bottom flask equipped with a stir bar was added 2-(2,6-dichloro-phenylamino)-1,6,7-trimethyl-1,8-dihydro-imidazo[4,5-h]isoquinolin-9-one (2.4 g, 6.2 mmol), selenium dioxide (2.0 g, 18 mmol) and dioxane (150 mL). The flask was fitted with a condenser and heated to reflux for 4.5 h. The reaction was then removed from heat and allowed to cool to room temperature. The slightly opaque solution was filtered through celite and washed with dichloromethane:methanol (9:1). The solution was concentrated and the resulting residue triturated with dichloromethane to produce 2-(2,6-dichloro-phenylamino)-1,6-dimethyl-9-oxo-8,9-dihydro-1H-imidazo[4,5-h]isoquinoline-7-carbaldehyde (1.8 g, 72%) as a brownish yellow solid, which was used without further purification. 1H NMR (400 MHz, DMSO-d6+TFA) δ 10.65 (s, 1H), 10.24 (s, 1H), 7.96 (d, 1H, J=8.6 Hz), 7.78 (d, 1H, J=8.6 Hz), 7.70 (d, 2H, J=7.8 Hz), 7.49 (d, 2H, J=7.8 Hz), 4.15 (s, 3H), 2.70 (s, 3H); ESMS (m/z): found, 401.

후처리

  1. customTo a 200 mL round bottom flask equipped with a stir bar
  2. customThe flask was fitted with a condenser
  3. temperatureheated
  4. temperatureto reflux for 4.5 h
  5. customThe reaction was then removed
  6. temperaturefrom heat
  7. filtrationThe slightly opaque solution was filtered through celite
  8. washwashed with dichloromethane:methanol (9:1)
  9. concentrationThe solution was concentrated
  10. customthe resulting residue triturated with dichloromethane

출처 및 근거

ORD 기록
ord-224581463b83459aa11c3666eefceecd
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067395B2

반응 노트

불러오는 중…