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

HRID 1398420노트

반응식

HRID 1398420 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-188646fe07af48278ef7b964391dacd7
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901305B2

반응 노트

불러오는 중…