3-butyryl-8-phthalimido-4(1H)quinolone → 3-Butyryl-4-chloro-8-phthalimidoquinoline

HRID 1090670Notes

Reaction equation

HRID 1090670 reaction equation
[C:1]([C:6]1[C:15](=O)[C:14]2[C:9](=[C:10]([N:17]3[C:21](=[O:22])[C:20]4=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]4[C:18]3=[O:27])[CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)(O[Cl:31])=O>>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:31])=[CH:13][CH:12]=[CH:11][C:10]=2[N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 103385613-butyryl-8-phthalimido-4(1H)quinoloneHCID 86587839Phosphoryloxychloride

Product 1

HCID 100910853-Butyryl-4-chloro-8-phthalimidoquinolineYield 57%

Procedure

3-Butyryl-8-phthalimido-4(1H)quinolone (36 g, 0.1 mol) was heated under reflux in phosphoryl oxychloride (200 ml) for 1 hour. The solvent was evaporated and the residue dissolved in chloroform and poured into a rapidly stirred mixture of ice, water and ammonia then stirred for 10 minutes. The chloroform layer was washed with brine, dried (anhyd. MgSO4), filtered and evaporated to a brown oil. Chromatography (silica gel/5% methanol in chloroform) gave 3-butyryl-4-chloro-8-phthalimidoquinoline as a light brown oil (21.5g, 57%).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in chloroform
  3. additionpoured into a rapidly stirred mixture of ice, water and ammonia
  4. washThe chloroform layer was washed with brine
  5. dry with materialdried (anhyd. MgSO4)
  6. filtrationfiltered
  7. customevaporated to a brown oil

Sources & evidence

ORD record
ord-60d71638c7fc484bbe1065699fec7e99
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

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