Selenium Dioxide → 8-Chloro-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridine-4-carbaldehyde

HRID 1398420ノート

反応式

HRID 1398420 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[C:10]([CH3:15])[N:11]=[CH:12][CH:13]=3)[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1.[Se](=O)=[O:20]>CC(O)=O.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[C:10]([CH:15]=[O:20])[N:11]=[CH:12][CH:13]=3)[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1

参加物

5

反応物 2

HCID 24007Selenium DioxideHCID 867103378-Chloro-4,6-dimethyl-5H,6H-benzo[c]2,7-naphthyridin-5-one

生成物 1

HCID 867104098-Chloro-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridine-4-carbaldehyde収率 52.2%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

To a solution of 8-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (100 mg, 0.387 mmol), prepared as described in Example 16, Part G, in AcOH (4 mL) was added selenium dioxide (51.5 mg, 0.464 mmol). The reaction mixture was allowed to stir at 70° C. for 3 h. Volatiles were removed under reduced pressure and the residue so obtained was dissolved in dichloromethane (2 mL). The mixture was filtered through diatomaceous earth (Celite®) and the filtrate was concentrated under reduced pressure to afford the title product (0.1 g, 0.202 mmol, 52% crude yield) as pale yellow solid. The material was carried on without further purification. LC/MS, (ESI) m/z 273.0 [(M+H)+, calcd for C14H10ClN2O2, 273.0]; LC/MS retention time (method H): tR=1.89 min.

後処理

  1. customVolatiles were removed under reduced pressure
  2. customthe residue so obtained
  3. filtrationThe mixture was filtered through diatomaceous earth (Celite®)
  4. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-188646fe07af48278ef7b964391dacd7
出典データセット
uspto-grants-2014_12
特許番号
US08901305B2

反応ノート

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