Potassium Nitrate → 4-Hydroxy-3,6-dinitro-2(1H)-quinolinone

HRID 54414Notes

Reaction equation

HRID 54414 reaction equation
[N+:1]([C:4]1[C:5](=[O:15])[NH:6][C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].[N+:16]([O-])([O-:18])=[O:17].[K+]>OS(O)(=O)=O>[N+:1]([C:4]1[C:5](=[O:15])[NH:6][C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][C:10]([N+:16]([O-:18])=[O:17])=[CH:9][CH:8]=2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 546801624-Hydroxy-3-nitro-2(1H)-quinolinone

Product 1

HCID 546964714-Hydroxy-3,6-dinitro-2(1H)-quinolinoneYield 68.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 724 mg (3.51 retool) of 3-nitro-4-hydroxy-1,2-dihydroquinolin-2-one and 401 mg (3.97 retool) of KNO3 in 4 mL of 96% H2SO4 was stirred in an ice-bath for 30 min, then 25° C. for 20 h. The solution was added into 25 mL of ice-water to give a yellow precipitate and the mixture was stirred for 1 h, filtered and washed with water, and dried to leave 602 mg (68%) of title compound as a yellow solid, mp 197°-198° C. (decomposed, lit (Buckle et al., supra) 199° -200° C.). 1H NMR (CDCl3 +DMSO-d6), 7.114 (d, 1, J=9.12), 7.980 (dd, 1, J=2.27, 9.13), 8.628 (d, 1, J=2.28), 12.13 (mb, 1).

Workup

  1. customto give a yellow precipitate
  2. filtrationfiltered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-86c483a31b3040f290ba976e0bfb7aad
Source dataset
uspto-grants-1997_04
Patent number
US05622965

Reaction notes

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