1,4-Dioxane → 7-Formyl-4-phenylquinoline-2-carbonitrile

HRID 2422526Notes

Reaction equation

HRID 2422526 reaction equation
Br[CH:2](Br)[C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:8][C:9]([C:13]#[N:14])=[N:10]2)=[CH:5][CH:4]=1.[O:22]1CCOCC1>O.CCOC(C)=O.[N+]([O-])([O-])=O.[Ag+]>[CH:2]([C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:8][C:9]([C:13]#[N:14])=[N:10]2)=[CH:5][CH:4]=1)=[O:22]

Participants

6

Reactant 2

HCID 312751,4-DioxaneHCID 667902487-(Dibromomethyl)-4-phenylquinoline-2-carbonitrile

Product 1

HCID 574378457-Formyl-4-phenylquinoline-2-carbonitrile

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-(dibromomethyl)-4-phenylquinoline-2-carbonitrile (2.02 g, 4.81 mmol) in 1,4-dioxane (75 mL) was added a solution of silver nitrate (3.27 g, 19.24 mmol) in 30 mL of water, and the reaction mixture stirred 1 h at reflux. After cooling to rt, the mixture was diluted with EtOAc and filtered. The solid was washed with EtOAc and the organic phases combined. The filtrate was washed twice with water and the combined aqueous layers were back-extracted twice with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography (eluting with acetone-CH2Cl2-toluene, 10:40:50) to yield the title compound. 1H NMR (400 MHz, acetone-d6): δ 10.39 (s, 1H), 8.80 (s, 1H), 8.21 (s, 2H), 8.07 (s, 1H), 7.66 (m, 5H).

Workup

  1. temperatureat reflux
  2. filtrationfiltered
  3. washThe solid was washed with EtOAc
  4. washThe filtrate was washed twice with water
  5. extractionthe combined aqueous layers were back-extracted twice with EtOAc
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue obtained
  11. customwas purified by column chromatography (eluting with acetone-CH2Cl2-toluene, 10:40:50)

Sources & evidence

ORD record
ord-76026457846243138282583150962968
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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