Toluene → HCID 22936402, compound

HRID 387712Notes

Reaction equation

HRID 387712 reaction equation
[NH2:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20]COC)=[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.[F:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]=[C:41]=[O:42])=[CH:36][CH:35]=1>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:24]=[CH:25][C:2]([NH:1][C:41]([NH:40][C:37]2[CH:38]=[CH:39][C:34]([F:33])=[CH:35][CH:36]=2)=[O:42])=[CH:3][CH:4]=1)#[N:18]

Participants

5

Reactant 3

HCID 1140TolueneHCID 709554-Fluorophenyl isocyanateHCID 229365064-(4-Aminophenoxy)-6-cyano-7-(2-methoxyethoxy)quinoline

Product 1

HCID 22936402HCID 22936402, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(4-Aminophenoxy)-6-cyano-7-methoxyethoxyquinoline (150 mg) was added to 5.0 ml of toluene and 2.5 ml of acetonitrile, and the mixture was heated to reflux. After then adding 4-fluorophenyl 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 150 mg of the title compound as light brown crystals (68% 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-588a2d832001474186f9688bcd750c87
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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