Phosphorus oxychloride → HCID 19922999, compound

HRID 1647451Notes

Reaction equation

HRID 1647451 reaction equation
[C:1]([C:6]1[C:15](=O)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:17][O:18][C:19](=O)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)([Cl:29])=O>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:29])=[CH:13][C:12]([CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:11][CH:10]=2)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 10405519HCID 10405519, compound

Product 1

HCID 19922999HCID 19922999, compoundYield 67%

Procedure

3-Butyryl-6-(benzoyloxymethyl)-4(1H)-quinolone (30 g) was heated under reflux in phosphorus oxychloride (200 ml) for 30 minutes. The solvent was evaporated and the residue partitioned between dichloromethane and ammonia solution. The organic layer was washed successively .with sodium hydrogen carbonate solution and 50% brine. Dried (anhyd. MgSO4), filtered and evaporated to an oily solid which crystallized on trituration with petroleum ether to give 3-butyryl-4-chloro-6-(benzyloxymethyl)quinoline (21.2 g, 67%), m.p. 85°-6° C.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between dichloromethane and ammonia solution
  3. washThe organic layer was washed successively .with sodium hydrogen carbonate solution and 50% brine
  4. customDried (anhyd
  5. filtrationMgSO4), filtered
  6. customevaporated to an oily solid which
  7. customcrystallized on trituration with petroleum ether

Sources & evidence

ORD record
ord-799f1382b3744ffcb6654f51df35f244
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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