Nitric Acid → HCID 54703487, compound

HRID 127912Notes

Reaction equation

HRID 127912 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C:6]3[C:14]([OH:19])=[CH:15][C:16](=[O:18])[O:17][C:5]=3[C:4]=2[CH:3]=1.[N+:20]([O-])([OH:22])=[O:21].O.C(O)(C)C>C(O)(=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C:6]3[C:14]([OH:19])=[C:15]([N+:20]([O-:22])=[O:21])[C:16](=[O:18])[O:17][C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 3776IsopropanolHCID 54703484HCID 54703484, compound

Product 1

HCID 54703487HCID 54703487, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

0.02 Mole 9-chloro-5,6-dihydro-6-methyl-2,5-dioxo-2H-pyrano[3,2-c]quinoline-4-ol from Example 7 (5.6 g) is suspended in 25 ml of glacial acetic acid. 4 ml of nitric acid (d=1.40) are added dropwise at 25° C., while stirring, and the magma-like reaction batch is then heated for 60 minutes to 95° C. It is then cooled to 20° C. During cooling, 36 ml of a mixture of water and isopropanol (1:1) is added. The whole is then filtered. The filter residue is washed with water to neutrality and after washing with isopropanol and petroleum ether, it is dried. 5.5 g (85% of the theory) of a crystalline residue are obtained, the crystals of which have a melting point of 241°-243° C. (decomp.) after recrystallization from a mixture of isobutanol and dimethylformamide.

Workup

  1. customthe magma-like reaction batch
  2. temperatureis then heated for 60 minutes to 95° C
  3. temperatureDuring cooling
  4. filtrationThe whole is then filtered
  5. washThe filter residue is washed with water to neutrality
  6. washafter washing with isopropanol and petroleum ether, it
  7. customis dried
  8. custom5.5 g (85% of the theory) of a crystalline residue are obtained
  9. customafter recrystallization
  10. additionfrom a mixture of isobutanol and dimethylformamide

Sources & evidence

ORD record
ord-9d67383c36eb4caaab6564168f0dee49
Source dataset
uspto-grants-1981_03
Patent number
US04258046

Reaction notes

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