2-Nitrophenol → N-(4-Butylphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl}urea

HRID 1857166Notes

Reaction equation

HRID 1857166 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+]([O-])=O.[N+:25](C1C=CC=CC=1O)([O-])=O.[CH2:35]([C:39]1[CH:44]=[CH:43][C:42]([N:45]=[C:46]=[O:47])=[CH:41][CH:40]=1)[CH2:36][CH2:37][CH3:38]>C1(C)C=CC=CC=1>[CH2:35]([C:39]1[CH:44]=[CH:43][C:42]([NH:45][C:46]([NH:25][C:19]2[CH:20]=[CH:21][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:17][CH:18]=2)=[O:47])=[CH:41][CH:40]=1)[CH2:36][CH2:37][CH3:38]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 27963134-Butylphenyl isocyanateHCID 221326976,7-Dimethoxy-4-(2-nitrophenoxy)quinoline

Product 1

HCID 22132682N-(4-Butylphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolinyl)oxy]phenyl}ureaYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(2-aminophenoxy)quinoline (56 mg), which was obtained, analogously to Example 49, by reducing 6,7-dimethoxy-4-(2-nitrophenoxy)quinoline obtained in the same manner as described in Example 48, except that 2-nitrophenol was used in place of 4-nitrophenol, was dissolved in toluene (3 ml) with heat, 4-n-butylphenyl isocyanate (0.2 ml) was added, and the admixture was refluxed with heat for 30 minutes. The resulting residue was purified by chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 45 mg of the title compound (yield: 50%).

Workup

  1. customobtained in the same manner
  2. temperaturewith heat
  3. temperaturethe admixture was refluxed
  4. temperaturewith heat for 30 minutes
  5. customThe resulting residue was purified by chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-4d7ffb8cb31941cab6b331e987539a2e
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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