Sulfuric Acid → HCID 178517235, compound

HRID 266929Notes

Reaction equation

HRID 266929 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, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of 147 mg (0.616 mmol) of 5,7-dichloro-2,4-quinolinediol (15b) and 126 mg (1.82 mmol) of NaNO2 in 3 mL of 0.2N NaOH in an ice-bath was added dropwise 2 mL of aqueous 2N H2SO4. The mixture was stirred in the 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 17b 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

Sources & evidence

ORD record
ord-5ded427dcf574bc0b15e4b59ed7ff5a4
Source dataset
uspto-grants-1997_07
Patent number
US05652368

Reaction notes

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