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

HRID 562425ノート

反応式

HRID 562425 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-224581463b83459aa11c3666eefceecd
出典データセット
uspto-grants-2011_11
特許番号
US08067395B2

反応ノート

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