Triethylamine → HCID 20079222, compound

HRID 1654090Notes

Reaction equation

HRID 1654090 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Cl:12][CH2:13][CH2:14][C:15](Cl)=[O:16].C(N(CC)CC)C.[OH-].[Na+]>C(Cl)Cl>[Cl:12][CH2:13][CH2:14][C:15]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)=[O:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 119115-AminoquinolineHCID 14798Sodium HydroxideHCID 693643-Chloropropionyl chloride

Product 1

HCID 20079222HCID 20079222, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 60 ml of methylene chloride was dissolved 4.5 g of 5-aminoquinoline, and 10.5 g of 3-chloropropionyl chloride and 9 g of triethylamine were then added thereto. After the liquid was allowed to stand at room temperature overnight, a 1N aqueous sodium hydroxide solution was added to the liquid, and the latter was then extracted with methylene chloride. The extract was washed twice with an aqueous sodium bicarbonate solution, was then dried, and was concentrated to obtain crystals. The latter were washed with methylene chloride, and filtered to obtain 2.2 g of 5-(3-chloropropionamido)quinoline in a crystalline state.

Workup

  1. additionwere then added
  2. extractionthe latter was then extracted with methylene chloride
  3. washThe extract was washed twice with an aqueous sodium bicarbonate solution
  4. customwas then dried
  5. concentrationwas concentrated
  6. customto obtain crystals
  7. washThe latter were washed with methylene chloride
  8. filtrationfiltered

Sources & evidence

ORD record
ord-3e31571250074bd981c811cb9577dd6a
Source dataset
uspto-grants-1995_04
Patent number
US05405843

Reaction notes

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