Sulfuric Acid → Chinisatin

HRID 235284Notes

Reaction equation

HRID 235284 reaction equation
[OH:1][C:2]1[C:11]([OH:12])=[C:10]([OH:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.OS(O)(=O)=O>>[NH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10](=[O:13])[C:11](=[O:12])[C:2]1=[O:1]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 1785171312,3-dihydroxy-1H-quinolin-4-one

Product 1

HCID 2785183ChinisatinYield 67.1%

Conditions

Temperature
25 °C

Procedure

To a mixture of 335 mg (1.89 mmol) of 11a in 4 mL of aqueous 0.1N H2SO4 was added dropwise 10 mL of aqueous 0.2M KIO4 (2 mmol) at 25° C. The mixture was stirred at 25° C. for 2 h, filtered and washed with water, dried to leave 222 mg (67%) of 12a as an almost colorless solid, mp>250° C. 1H NMR (DMSO-d6), 7.043 (d, 1, J=8.4), 7.089 (t, 1, J=7.8), 7.232 (s, 2), 7.577 (t, 1, J=7.8), 7.735 (d, 1, J=7.5), 10.735 (s, 1). 1H NMR (DMSO-d6 +D2O), 7.043 (d, 1), 7.098 (t, 1), 7.577 (t, 1), 7.735 (d, 1). MS, 175 (20, M+), 147 (20), 119 (100), 92 (60). High resolution MS, Calcd for C9H5NO3 175.0267, found 175.0275.

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-d1ad3fdbc91e4e4e806a3e0439dfefc7
Source dataset
uspto-grants-1997_01
Patent number
US05597922

Reaction notes

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