Hexane → 6-methoxy-2H-1-oxa-9-aza-phenanthrene-3-carbonitrile

HRID 2273179Notes

Reaction equation

HRID 2273179 reaction equation
N12[CH2:8][CH2:7][N:4](CC1)CC2.[OH:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([C:19]=1[CH:20]=O)=[CH:17][C:16]([O:22][CH3:23])=[CH:15][CH:14]=2.[CH3:24]CCCCC.C(OCC)(=O)C>C(#N)C=C>[CH3:23][O:22][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]1[O:9][CH2:24][C:8]([C:7]#[N:4])=[CH:20][C:19]2=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 9237DabcoHCID 866715273-Hydroxy-6-methoxy-quinoline-4-carbaldehyde

Product 1

HCID 672467646-methoxy-2H-1-oxa-9-aza-phenanthrene-3-carbonitrileYield 78%

Reagents, catalysts & solvents 1

HCID 7855AcrylonitrileSolvent

Procedure

1,4-Diazabicyclo[2.2.2]octane (345 mg, 3.07 mmol, 0.25 eq) is added at room temperature to a stirred suspension of 3-hydroxy-6-methoxy-quinoline-4-carbaldehyde (2.5 g, 12.3 mmol, 1.0 eq) in acrylonitrile (25 mL) and the resulting mixture is heated under reflux for 60 hours. The reaction mixture is then cooled to room temperature and extracted with ethyl acetate (3×100 mL) and a 1N sodium hydroxide aqueous solution (50 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: hexane:ethyl acetate, 5:1, v/v) to afford 6-methoxy-2H-1-oxa-9-aza-phenanthrene-3-carbonitrile as a light yellow solid (2.3 g, 78% yield).

Workup

  1. temperaturethe resulting mixture is heated
  2. temperatureunder reflux for 60 hours
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic layers are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue that
  8. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-319b1479eed0433380221d55f5c78d40
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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