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

HRID 1422890Notes

Reaction equation

HRID 1422890 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-7cad9b36509647fbb70874959c36184a
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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