Ammonium nitrate → 4-Hydroxy-7-methoxy-6-nitroquinoline-3-carbonitrile

HRID 548406Notes

Reaction equation

HRID 548406 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:15])[C:8]([C:13]#[N:14])=[CH:9][NH:10]2)=[CH:5][CH:4]=1.[N+:16]([O-])([O-:18])=[O:17].[NH4+]>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:15])[C:8]([C:13]#[N:14])=[CH:9][NH:10]2)=[CH:5][C:4]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 22985Ammonium nitrateHCID 125594304-Hydroxy-7-methoxyquinoline-3-carbonitrile

Product 1

HCID 109777094-Hydroxy-7-methoxy-6-nitroquinoline-3-carbonitrileYield 44.4%

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideSolvent

Procedure

To a suspension of 10 g (49.6 mmol) of 1,4-dihydro-7-methoxy-4-oxo-quinoline-3-carbonitrile in 160 ml of trifluroacetic anhydride was added 6 g (74.9 mmol) of ammonium nitrate over a period of 3 hours. The mixture was stirred an additional two hours. Excess anhydride was removed at reduced pressure at 45° C. The residue was stirred with 500 ml of water. The solid was collected and washed with water. The solid was dissolved in 1000 ml of boiling acetic acid and the solution was treated with decolorizing charcoal. The mixture was filtered and concentrated to a volume of 300 ml. Cooling gave a solid which was collected giving 5.4 g of 1,4-dihydro-7-methoxy-6-nitro-4-oxo-quinoline-3-carbonitrile as a brown solid: mass spectrum (electrospray, m/e): M+H 246.

Workup

  1. customExcess anhydride was removed at reduced pressure at 45° C
  2. stirringThe residue was stirred with 500 ml of water
  3. customThe solid was collected
  4. washwashed with water
  5. dissolutionThe solid was dissolved in 1000 ml of boiling acetic acid
  6. additionthe solution was treated with decolorizing charcoal
  7. filtrationThe mixture was filtered
  8. concentrationconcentrated to a volume of 300 ml
  9. temperatureCooling
  10. customgave a solid which
  11. customwas collected

Sources & evidence

ORD record
ord-76d0373a103e4d16a4c68a5518e67322
Source dataset
uspto-grants-2011_05
Patent number
USRE042376E1

Reaction notes

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