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

HRID 1398420Notes

Reaction equation

HRID 1398420 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-188646fe07af48278ef7b964391dacd7
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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