3-Nitrophenol → HCID 22132751, compound

HRID 1857167Notes

Reaction equation

HRID 1857167 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]=[C:18]([N+:22]([O-])=O)[CH:17]=1.[N+](C1C=C(O)C=CC=1)([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:22][C:18]2[CH:19]=[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]=2)=[O:47])=[CH:41][CH:40]=1)[CH2:36][CH2:37][CH3:38]

Participants

5

Reactant 3

HCID 111373-NitrophenolHCID 27963134-Butylphenyl isocyanateHCID 22132767HCID 22132767, compound

Product 1

HCID 22132751HCID 22132751, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6,7-Dimethoxy-4-(3-aminophenoxy)quinoline (51 mg), which was obtained, analogously to Example 49, by reducing 6,7-dimethoxy-4-(3-nitrophenoxy)quinoline obtained in the same manner as described in Example 48, except that 3-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 50 minutes. The resulting residue was purified by chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 26 mg of the title compound (yield: 32%).

Workup

  1. customobtained in the same manner
  2. temperaturewith heat
  3. temperaturethe admixture was refluxed
  4. temperaturewith heat for 50 minutes
  5. customThe resulting residue was purified by chromatography on silica gel eluting with chloroform/acetone (10/1)

Sources & evidence

ORD record
ord-af2f59cf75454b6aa9d9f1dae4485329
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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