Sulfuric Acid → HCID 178517235, compound

HRID 235282Notes

Reaction equation

HRID 235282 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4]([OH:14])=[CH:5][C:6]([OH:13])=[N:7]2.[N:15]([O-])=[O:16].[Na+].OS(O)(=O)=O>[OH-].[Na+]>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:14])[C:5](=[N:15][OH:16])[C:6](=[O:13])[NH:7]2

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 23668193Sodium NitriteHCID 178516558HCID 178516558, compound

Product 1

HCID 178517235HCID 178517235, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of 147 mg (0.616 mmol) of 5,7-dichloro-2,4-quinolinediol and 126 mg (1.82 mmol) of NaNO2 in 3 mL of 0.2N NaOH in ice-bath was added dropwise 2 mL of aqueous 2N H2SO4. The mixture was stirred in ice-bath for 4 h after addition of H2SO4, filtered and dried to leave an orange solid. The solid was crystallized by boiling with 10 mL of ethanol (95% ). The solution was cooled to room temperature, filtered and dried to leave 132 mg (83%) of 5,7-dichloro-3-oximequinoline-2,4-dione as a yellow solid, mp 244°-245° C. (decomposed). 1H NMR (CDCl3 +DMSO-d6), 7.011 (d, 0.44, J=1.8) 7.080 (m, 1.54), 11.567 (sb, 0.35), 11.821 (s, 0.46). MS, 258 (100, M+), 241 (60), 214 (80), 187 (20), 160 (30). High resolution MS, Calcd for C9H435Cl2N2O3, 257.9595, found 257.9598.

Workup

  1. filtrationfiltered
  2. customdried
  3. customto leave an orange solid
  4. customThe solid was crystallized
  5. filtrationfiltered
  6. customdried
  7. customto leave 132 mg (83%) of 5,7-dichloro-3-oximequinoline-2,4-dione as a yellow solid, mp 244°-245° C. (decomposed)

Sources & evidence

ORD record
ord-f40d0684318c44838288e485ac873e9c
Source dataset
uspto-grants-1997_01
Patent number
US05597922

Reaction notes

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