Toluene → HCID 22936933, compound

HRID 1433361Notes

Reaction equation

HRID 1433361 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[CH2:30]([N:34]=[C:35]=[O:36])[CH2:31][CH2:32][CH3:33]>C(#N)C>[C:17]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:19][CH3:20])[N:10]=[CH:9][CH:8]=[C:7]2[O:6][C:5]1[CH:21]=[CH:22][C:2]([NH:1][C:35]([NH:34][CH2:30][CH2:31][CH2:32][CH3:33])=[O:36])=[CH:3][CH:4]=1)#[N:18]

Participants

5

Reactant 3

HCID 1140TolueneHCID 8110Butyl isocyanateHCID 22936407HCID 22936407, compound

Product 1

HCID 22936933HCID 22936933, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(4-Aminophenoxy)-6-cyano-7-methoxyquinoline (150 mg) was added to 2.5 ml of toluene and 2.5 ml of acetonitrile, and the mixture was heated to reflux. After then adding n-butyl isocyanate (0.12 ml), the mixture was further heated to reflux for 1 hour. After cooling, the precipitated solid was filtered out and washed with ethyl acetate/toluene=1/1 to obtain 110 mg of the title compound as light brown crystals (55% yield).

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid was filtered out
  5. washwashed with ethyl acetate/toluene=1/1

Sources & evidence

ORD record
ord-822fdb3ed15e4ba0bf2a4249cd2ceac7
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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