Dimethylamine → HCID 67133729, compound

HRID 1949165Notes

Reaction equation

HRID 1949165 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][NH:8][CH3:9].[CH2:10]([O:12][C:13]([C:15]1[C:16]([S:27][CH2:28][CH3:29])=[N:17][C:18]2[C:23]([C:24]=1[CH3:25])=[CH:22][CH:21]=[C:20](F)[CH:19]=2)=[O:14])[CH3:11].CCCCCC>CCO>[CH2:10]([O:12][C:13]([C:15]1[C:16]([S:27][CH2:28][CH3:29])=[N:17][C:18]2[C:23]([C:24]=1[CH3:25])=[CH:22][CH:21]=[C:20]([N:8]([CH3:9])[CH3:7])[CH:19]=2)=[O:14])[CH3:11]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8058HexaneHCID 11430Potassium CarbonateHCID 67133617HCID 67133617, compound

Product 1

HCID 67133729HCID 67133729, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

2.8 g (20.5 mmol) K2CO3 and a 40% aq. dimethylamine solution (20.5 ml) were added to a solution of 2.0 g (6.8 mmol) 2-ethylsulfanyl-7-fluoro-4-methyl-quinoline-3-carboxylic acid ethyl ester in EtOH (20 ml) and the mixture was heated for 16 h at 90° C. in a closed vessel. Then the reaction solution was concentrated to small volume under vacuum and the residue was taken up with water. It was then extracted with EE. The organic phase was washed with water and brine, dried over Na2SO4, filtered and concentrated to small volume under vacuum. Column chromatography (hexane/EE 25:1) of the residue yielded 810 mg (2.55 mmol, 38%) 7-dimethylamino-2-ethylsulfanyl-4-methyl-quinoline-3-carboxylic acid ethyl ester.

Workup

  1. concentrationThen the reaction solution was concentrated to small volume under vacuum
  2. extractionIt was then extracted with EE
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-04092b60a9b145c394778eaf8a31cc20
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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