Nitric Acid → HCID 70275766, compound

HRID 1901468Notes

Reaction equation

HRID 1901468 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[C:4](=[O:13])[CH2:5][CH:6]=[N:7]2.[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[CH3:1][C:2]1[C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[C:4](=[O:13])[CH2:5][CH:6]=[N:7]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 70279916HCID 70279916, compound

Product 1

HCID 70275766HCID 70275766, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

In a flask is placed 5,8-dimethyl-4-quinolone (5.18 g, 29.9 mmol) (prepared according to Burckhalter, et al., J. Am. Chem. Soc., Vol. 70 (1948), p. 1363) with sulfuric acid (30 mL). After stirring for 10 minutes, the flask is cooled in ice and concentrated nitric acid (1.90 mL, 30.2 mmol) is added dropwise. After the addition is completed, the mixture is stirred for 15 minutes in ice. The mixture is then poured onto crushed ice and allowed to warm to room temperature. The gray solid is filtered and washed with water. The solid is recrystallized from hot methanol to give 5,8-dimethyl-6-nitro-4-quinolone.

Workup

  1. customIn a flask is placed
  2. temperaturethe flask is cooled in ice
  3. additionAfter the addition
  4. stirringthe mixture is stirred for 15 minutes in ice
  5. additionThe mixture is then poured
  6. customonto crushed ice
  7. filtrationThe gray solid is filtered
  8. washwashed with water
  9. customThe solid is recrystallized from hot methanol

Sources & evidence

ORD record
ord-c896f4d23cf847858ac62bd203fcbd85
Source dataset
uspto-grants-1996_11
Patent number
US05578607

Reaction notes

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