Water → HCID 14724143, compound

HRID 2073215Notes

Reaction equation

HRID 2073215 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[N:16]1([NH2:21])[CH:20]=[CH:19][CH:18]=[CH:17]1.O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C>[ClH:1].[N:16]1([NH:21][C:2]2[C:11]3[C:6](=[CH:7][C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH:20]=[CH:19][CH:18]=[CH:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 676684-Chloro-7-(trifluoromethyl)quinolineHCID 1365891-Aminopyrrole

Product 1

HCID 14724143HCID 14724143, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-chloro-7-(trifluoromethyl)quinoline (5 g) and 1H-pyrrol-1-amine (2.1 g) in 100 ml of isopropanol containing 1 ml saturated ether/HCl was stirred for thirty minutes at reflux, and thereafter was cooled, stirred with water, basified with sodium carbonate and extracted with ether. The organic extract was washed successively with water and saturated sodium chloride solution, dried (anhy. MgSO4), filtered and concentrated to 6.5 g solid. This was converted to the hydrochloride salt and recrystallized twice from methanol/ether to give 2.4 g white crystals, 260° dec.

Workup

  1. temperatureat reflux
  2. temperaturewas cooled
  3. extractionextracted with ether
  4. extractionThe organic extract
  5. washwas washed successively with water and saturated sodium chloride solution
  6. customdried (anhy
  7. filtrationMgSO4), filtered
  8. concentrationconcentrated to 6.5 g solid
  9. customrecrystallized twice from methanol/ether

Sources & evidence

ORD record
ord-83691bb49f6a4e25b3f5b368bd665a00
Source dataset
uspto-grants-1990_04
Patent number
US04916135

Reaction notes

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