Water → HCID 14724139, compound

HRID 2073214Notes

Reaction equation

HRID 2073214 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:12][N:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C>[ClH:1].[N:13]1([NH:12][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 691404-ChloroquinolineHCID 1365891-Aminopyrrole

Product 1

HCID 14724139HCID 14724139, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-chloroquinoline (10 g) and 1-aminopyrrole (6 g) in 100 ml isopropanol containing 1 ml saturated ether/HCl was stirred at 80° for thirty minutes, and thereafter cooled, stirred with water, basified with sodium carbonate and extracted with dichloromethane. The organic extract was washed successively with water and saturated sodium chloride solution, dried (anhy. MgSO4), filtered and concentrated to 12 g of solid, m.p. 165°-168°. Four grams were converted to the hydrochloride salt and recrystallized twice from methanol/ether to give 2.9 g crystals, m.p. 233°-234°.

Workup

  1. temperaturecooled
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed successively with water and saturated sodium chloride solution
  5. customdried (anhy
  6. filtrationMgSO4), filtered
  7. concentrationconcentrated to 12 g of solid, m.p. 165°-168°
  8. customrecrystallized twice from methanol/ether

Sources & evidence

ORD record
ord-2e1468324d184def9d1aa76f77196ff5
Source dataset
uspto-grants-1990_04
Patent number
US04916135

Reaction notes

Loading…