Potassium Carbonate → HCID 17979837, compound

HRID 133096Notes

Reaction equation

HRID 133096 reaction equation
[N+:1]([C:4]1[CH:5]=[N+:6]([O-])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][C:8]=2[CH3:14])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].P(Cl)(Cl)([Cl:24])=O>C(OCC)(=O)C>[Cl:24][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:13][C:12]2[C:7](=[C:8]([CH3:14])[CH:9]=[CH:10][CH:11]=2)[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 179798513-Nitro-8-methyl-quinoline-1-oxide2×

Product 1

HCID 17979837HCID 17979837, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2.09 g of 3-nitro-8-methyl-quinoline-1-oxide (compound D1) in 15 ml of phosphorus oxychloride is stirred at 100° C. for 1 h. After cooling to room temperature, the reaction mixture is added to 40 ml of ice water and diluted with 50 ml of ethyl acetate. With the aid of solid potassium carbonate the pH value is adjusted to pH 8 and the mixture is extracted two times each with 30 ml of ethyl acetate. The combined organic phases are dried using magnesium sulfate, filtered and evaporated in vacuo. The residue is recrystallized from diethylether to give 1.3 g of the title compound as violet solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture is extracted two times each with 30 ml of ethyl acetate
  3. customThe combined organic phases are dried
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue is recrystallized from diethylether

Sources & evidence

ORD record
ord-b01c2f5c9e684015a3544beb04567c5e
Source dataset
uspto-grants-2008_06
Patent number
US07390819B2

Reaction notes

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