Nitric Acid → 6, 7-Dichloro-3-nitro-4-hydroxy-1,2-dihydroquinolin-2-one

HRID 54415Notes

Reaction equation

HRID 54415 reaction equation
ClC1C(Cl)=CC=C2C=1C(O)=CC(O)=N2.[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[Cl:26])[N:22]=[C:21]([OH:27])[CH:20]=[C:19]2[OH:28].[N+:29]([O-])([OH:31])=[O:30]>C(O)(=O)C>[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][C:25]=1[Cl:26])[NH:22][C:21](=[O:27])[C:20]([N+:29]([O-:31])=[O:30])=[C:19]2[OH:28]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 178516556HCID 178516556, compoundHCID 178516559HCID 178516559, compound

Product 1

HCID 547033996, 7-Dichloro-3-nitro-4-hydroxy-1,2-dihydroquinolin-2-oneYield 19%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 1.25 g (5.43 mmol) of 5,6-dichloro-2,4-dihydroxyquinoline and 6,7-dichloro-2,4-dihydroxyquinoline in 8 mL of glacial acetic acid was added 1.5 mL of HNO3 (69-71%) and the mixture was heated at 90° C. for 2 h. The mixture was cooled to room temperature, filtered and washed with water, and dried to leave 280 mg (19%) of the title compound as a yellow solid, mp 235°-236° C. (decomposed). 1H NMR (CDCl3 +DMSO-d6), 7.362 (s, 1), 8.039 (s, 1), 11.369 (s, 1). MS, 274 (50, M+), 214 (100), 187 (18), 160 (20). High resolution MS, Calcd for C9H435Cl2N2O4 273.9544, found 273.9548.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-31f056ac902a4db58895c80539445be8
Source dataset
uspto-grants-1997_04
Patent number
US05622965

Reaction notes

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