Phosphorus oxychloride → HCID 19592834, compound

HRID 613502Notes

Reaction equation

HRID 613502 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13](C(=NO)C)=[CH:12]2)=[O:5].P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:4]([NH:6][C:13]1[CH:14]=[N:15][C:16]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6][C:4](=[O:5])[C:3]1[C:2]([Cl:1])=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:25])(=[O:5])[CH3:3]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 85729257HCID 85729257, compound

Product 1

HCID 19592834HCID 19592834, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 8-(2,6-dichlorobenzoylamino)-3-(1-hydroxyiminoethyl)quinoline (168 mg) in pyridine was added phosphoryl chloride (516 mg) at 4° C., and the mixture was stirred for 50 minutes at the same temperature. The mixture was poured into ice and extracted with dichloromethane. The organic layer was washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethanol and water to give 3-acetylamino-8-(2,6-dichlorobenzoylamino)quinoline (19 mg).

Workup

  1. additionThe mixture was poured into ice
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from ethanol and water

Sources & evidence

ORD record
ord-ddd4ad7311dd4c1ab88898ca614570fe
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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