Triethylamine → 2-chloro-N,N-dimethylquinoline-4-carboxamide

HRID 2415130Notes

Reaction equation

HRID 2415130 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](Cl)=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:15]([N:17](CC)[CH2:18]C)C.Cl.CNC>C(Cl)(Cl)Cl>[CH3:15][N:17]([CH3:18])[C:12]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([Cl:1])[CH:11]=1)=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 754382-Chloroquinoline-4-carbonyl chloride

Product 1

HCID 430827022-chloro-N,N-dimethylquinoline-4-carboxamideYield 40%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of the resultant 2-chloroquinoline-4-carbonyl chloride in chloroform (50 ml) was treated with triethylamine (4.4 ml, 31.5 mmol), followed by solid dimethylamine hydrochloride (1.28 g, 15.7 mmol). The reaction stirred for one hour at ambient temperature at which time it was washed with 10% aqueous sodium hydroxide and 15% aqueous citric acid. Drying over anhydrous sodium sulfate, followed by evaporation under reduced pressure gave 2-chloroquinoline-4-carboxylic acid dimethylamide (1.5 g, 40%) as a tan solid. [M+H]+ 235.

Workup

  1. washwas washed with 10% aqueous sodium hydroxide and 15% aqueous citric acid
  2. dry with materialDrying over anhydrous sodium sulfate
  3. customfollowed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-5cf059266b9d45e5887c510f88d9c13c
Source dataset
uspto-grants-2004_11
Patent number
US06818655B2

Reaction notes

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