Water → HCID 14986013, compound

HRID 2051473Notes

Reaction equation

HRID 2051473 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[N+:9]([O-])[C:10]3[C:15]([C:16]=2[N+:17]([O-:19])=[O:18])=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:3][CH2:2]1.[C:21]1([N:27]=C=O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CN(C)C=O>[NH:27]([C:8]1[C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[C:16]([N+:17]([O-:19])=[O:18])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7672Phenyl isocyanateHCID 14986012HCID 14986012, compound

Product 1

HCID 14986013HCID 14986013, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 3-morpholino-4-nitroquinoline-N-oxide (3 g, 0.011 mol) was suspended in dimethylformamide (40 ml) and following addition of phenyl isocyanate (3.4 g, 0.029 mol), the mixture was added on an oil bath at 80°-90° C. for ca. 3 hours. The reaction mixture was totally charged into water and subjected to extraction with chloroform. The chloroform layer was washed with water and dried with anhydrous sodium sulfate. After the chloroform was distilled off under vacuum, the residue was subjected to recrystallization with ethanol. The resulting crystal was recovered by filtration under vacuum to obtain 2-anilino-3-morpholino-4-nitroquinoline in an amount of 2.95 g (yield, 77%).

Workup

  1. additionthe mixture was added on an oil bath at 80°-90° C. for ca. 3 hours
  2. extractionsubjected to extraction with chloroform
  3. washThe chloroform layer was washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationAfter the chloroform was distilled off under vacuum
  6. customthe residue was subjected to recrystallization with ethanol
  7. filtrationThe resulting crystal was recovered by filtration under vacuum

Sources & evidence

ORD record
ord-9cc7f4d6b4b74e54a5ab588edc807c17
Source dataset
uspto-grants-1991_05
Patent number
US05019574

Reaction notes

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