Quinoline → HCID 15572315, compound

HRID 2286583Notes

Reaction equation

HRID 2286583 reaction equation
C([S:4][C:5]1[NH:6][C:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:9]=1)C=C.N1C2C(=CC=CC=2)[CH:27]=[CH:26][CH:25]=1.C(O[C:38](=[O:40])[CH3:39])(=O)C>>[C:38]([S:4][C:5]1[NH:6][C:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[C:9]=1[CH2:27][CH:26]=[CH2:25])(=[O:40])[CH3:39]

Participants

4

Reactant 3

HCID 7047QuinolineHCID 7918Acetic AnhydrideHCID 23461731HCID 23461731, compound

Product 1

HCID 15572315HCID 15572315, compound

Procedure

A solution of 3.6 g (0.01 mole) of 2-allylthio-4,5-bis(4-chlorophenyl)pyrrole in 20 ml acetic anhydride was added dropwise to 20 ml quinoline preheated at 170°. The mixture was kept at 170° an additional 45 minutes, then cooled. Most of the acetic acid, acetic anhydride and quinoline were removed by distillation under reduced pressure. The residue was chromatographed on 125 g of Silic AR CC-7, eluting with toluene, to give, after recrystallization from hexane/methyl cyclohexane, 2.7 g of white product, m.p. 131°-2°.

Workup

  1. custompreheated at 170°
  2. temperaturecooled
  3. customMost of the acetic acid, acetic anhydride and quinoline were removed by distillation under reduced pressure
  4. customThe residue was chromatographed on 125 g of Silic AR CC-7
  5. washeluting with toluene
  6. customto give
  7. customafter recrystallization from hexane/methyl cyclohexane, 2.7 g of white product, m.p. 131°-2°

Sources & evidence

ORD record
ord-8046806887a7480fb37de9d6c497cdc2
Source dataset
uspto-grants-1981_05
Patent number
US04267184

Reaction notes

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