Nitric Acid → HCID 178486766, compound

HRID 81978Notes

Reaction equation

HRID 81978 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[C:10]([C:11]2[CH:20]=[C:19]3[C:14]([C:15](=[O:21])[CH:16]=[CH:17][NH:18]3)=[CH:13][C:12]=2[O:22][CH3:23])=[C:9]([CH3:24])[O:8][N:7]=1>C(O)(=O)CC>[CH3:5][C:6]1[C:10]([C:11]2[CH:20]=[C:19]3[C:14]([C:15]([OH:21])=[C:16]([N+:1]([O-:4])=[O:2])[CH:17]=[N:18]3)=[CH:13][C:12]=2[O:22][CH3:23])=[C:9]([CH3:24])[O:8][N:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 68187810HCID 68187810, compound

Product 1

HCID 178486766HCID 178486766, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 1032Propionic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Nitric acid (1.86 g, 1.32 ml, 29.5 mmol) was added dropwise to a stirred solution of 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-4(1H)-quinolinone (for a preparation see Intermediate 6) (6.9 g, 25.6 mmol) in propionic acid (70 ml). After complete addition the reaction mixture was stirred at 100° C. for 1 h. The reaction mixture was cooled to room temperature, the solid was filtered off, washed with diethyl ether and dried to give 7-(3,5-dimethyl-4-isoxazolyl)-6-(methyloxy)-3-nitro-4-quinolinol (5.0 g, 15.86 mmol, 62.1% yield) as a bright yellow solid. LCMS (formate) Rt 1.15 min, MH+ 316

Workup

  1. additionAfter complete addition the reaction mixture
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe solid was filtered off
  4. washwashed with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-5ac2a8f036cf40bea700709dce16227b
Source dataset
uspto-grants-2014_09
Patent number
US08846709B2

Reaction notes

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