Pyridine → HCID 178526754, compound

HRID 2051479Notes

Reaction equation

HRID 2051479 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.N1C=CC=CC=1.C(OC(=O)C)(=[O:29])C>>[OH:29][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

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14986012HCID 14986012, compound

Product 1

HCID 178526754HCID 178526754, compound

Procedure

The 3-morpholino-4-nitroquinoline-N-oxide obtained in Example 5-(a) was dissolved in acetic anhydride (16 ml) and pyridine (16 ml) and the solution was heated on an oil bath at 80° C. for 1 hour. Excess acetic anhydride and pyridine were distilled off under vacuum from the whole reaction mixture and the residue was dissolved in chloroform, followed by washing with 10% NaHCO3. The insoluble matter was recovered by filtration under vacuum, dissolved in acetone and treated with charcoal. The chloroform layer was dried with anhydrous Na2SO4 and CHCl3 was distilled off under vacuum. The residue was combined with the charcoal treated (insoluble) matter and washed with ethanol to obtain 2-hydroxy-3-morpholino-4-nitroquinoline in an amount of 3.5 g (yield, 44%).

Workup

  1. distillationExcess acetic anhydride and pyridine were distilled off under vacuum from the whole reaction mixture
  2. dissolutionthe residue was dissolved in chloroform
  3. washby washing with 10% NaHCO3
  4. filtrationThe insoluble matter was recovered by filtration under vacuum
  5. dissolutiondissolved in acetone
  6. additiontreated with charcoal
  7. dry with materialThe chloroform layer was dried with anhydrous Na2SO4 and CHCl3
  8. distillationwas distilled off under vacuum
  9. additiontreated (insoluble) matter
  10. washwashed with ethanol

Sources & evidence

ORD record
ord-e6f0840495304881b1e4cd914662b301
Source dataset
uspto-grants-1991_05
Patent number
US05019574

Reaction notes

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