Sulfuric Acid → HCID 178517130, compound

HRID 235281Notes

Reaction equation

HRID 235281 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N:13]([O-])=[O:14].[Na+].OS(O)(=O)=O>[OH-].[Na+]>[N:13](=[C:11]1[C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2]1=[O:1])[OH:14]

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 23668193Sodium NitriteHCID 1785165532-hydroxy-1H-quinolin-4-one

Product 1

HCID 178517130HCID 178517130, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of 3.21 g (19.9 mmol) of 2,4-dihydroxyquinoline and 1.87 g (27.1 mmol) of NaNO2 in 60 mL of 0.2N NaOH in an ice-bath was added dropwise 40 mL of aqueous 2N H2SO4. The mixture was stirred in an ice bath for 1 h after addition of H2SO4, filtered and dried to leave 3.41 g of orange solid which was crystallized by boiling with 150 mL of ethanol (95%) and filtered. The filtrate was cooled to and kept at room temperature for 5 h. The crystalline precipitate was filtered and dried to leave 1.88 g (50%) of 10a as a red solid, mp 206° C. (decomposed, lit 208° C., dec.). 1H NMR (CDCl3 +DMSO-d6), 6.65-6.78 (m, 2), 7.15 (m, 1), 7.556 (d, 0.30, J=8.1), 7.605 (d, 0.70, J=8.1), 10.887 (s, 0.3), 11.346 (s, 0.7). MS, 190 (100, M+), 173 (25), 146 (55). High resolution MS, Calcd for C9H6N2O3, 190.0375, found 190.0400.

Workup

  1. filtrationfiltered
  2. customdried

Sources & evidence

ORD record
ord-89fcbe0d4dbd4c1f89c4c4bb271ca0ae
Source dataset
uspto-grants-1997_01
Patent number
US05597922

Reaction notes

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