Phosphorus oxychloride → HCID 19592815, compound

HRID 613453Notes

Reaction equation

HRID 613453 reaction equation
[C:1]([C:4]1[C:13](=O)[C:12]2[C:7](=[C:8]([N+:15]([O-:17])=[O:16])[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].P(Cl)(Cl)([Cl:20])=O>>[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[Cl:20])=[CH:11][CH:10]=[CH:9][C:8]=2[N+:15]([O-:17])=[O:16])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 19593006HCID 19593006, compound

Product 1

HCID 19592815HCID 19592815, compound

Conditions

Temperature
115 °C

Procedure

A mixture of 3-acetyl-1,4-dihydro-8-nitro-4-oxoquinoline (500 mg) and phosphoryl chloride was heated at 115° C. for 15 minutes. After cooling, the mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo to give 3-acetyl-4-chloro-8-nitroquinoline (485 mg).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-59c7f20002d943eb9c8ee4cbf27d1640
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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