2,6-Lutidine → 8-Chloro-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridine-9-carbaldehyde

HRID 1398365Notes

Reaction equation

HRID 1398365 reaction equation
[Cl:1][C:2]1[C:3]([CH:19]=C)=[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.CC1C=CC=C(C)N=1.I([O-])(=O)(=O)=[O:30].[Na+]>O1CCOCC1.O.C(OCC)(=O)C.[Os](=O)(=O)(=O)=O>[Cl:1][C:2]1[C:3]([CH:19]=[O:30])=[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

Participants

8

Reactant 3

HCID 79372,6-LutidineHCID 23667635Sodium periodateHCID 867103588-chloro-4,6-dimethyl-9-vinylbenzo[c][2,7]naphthyridin-5(6H)-one

Product 1

HCID 867103598-Chloro-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridine-9-carbaldehydeYield 100%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 8-chloro-4,6-dimethyl-9-vinylbenzo[c][2,7]naphthyridin-5(6H)-one (600 mg, 2.107 mmol), osmium tetroxide (2.5% in 2-methyl-2-propanol) (0.794 mL, 0.063 mmol), and 2,6-dimethylpyridine (0.491 mL, 4.21 mmol) in 1,4-dioxane (30 mL) and water (30 mL) cooled to 0° C. was added sodium periodate (1803 mg, 8.43 mmol). The mixture was warmed to room temperature and stirred for 3 h. The mixture was diluted with ethyl acetate and filtered through diatomaceous earth (Celite®). The organic layer was concentrated under reduced pressure to afford a brown solid. The solid was washed with hexane (3×20 mL) and dried under vacuum to afford 8-chloro-4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridine-9-carbaldehyde 0.6 g, 2.107 mmol, 84% yield) as a gummy brown solid. LC/MS (ESI) m/e 287.0 [(M+H)+, calcd for C15H12ClN2O2, 287.1]; LC/MS retention time (method B): tR=2.03 min.

Workup

  1. filtrationfiltered through diatomaceous earth (Celite®)
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customto afford a brown solid
  4. washThe solid was washed with hexane (3×20 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f6d0628a54a74a81a8835de42daaa081
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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