Water → 2-((Cyclobutylmethyl)(ethyl)amino)-8-methylquinoline-3-carbaldehyde

HRID 1911772Notes

Reaction equation

HRID 1911772 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:17]([CH:18]=[O:19])=[CH:16][C:15]2[C:10](=[C:11]([CH3:20])[CH:12]=[CH:13][CH:14]=2)[N:9]=1.[CH:21]1([CH2:25][NH:26][CH2:27][CH3:28])[CH2:24][CH2:23][CH2:22]1.O>CN(C)C=O.C(OCC)(=O)C>[CH:21]1([CH2:25][N:26]([CH2:27][CH3:28])[C:8]2[C:17]([CH:18]=[O:19])=[CH:16][C:15]3[C:10](=[C:11]([CH3:20])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6890822-Chloro-8-methylquinoline-3-carboxaldehydeHCID 23366322(Cyclobutylmethyl)(ethyl)amine

Product 1

HCID 574868422-((Cyclobutylmethyl)(ethyl)amino)-8-methylquinoline-3-carbaldehydeYield 75%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.62 g, 4.5 mmol) was added to a solution of 2-chloro-8-methyl-quinoline-3-carbaldehyde (0.45 g, 2.2 mmol) and cyclobutylmethyl-ethyl-amine (0.47 g, 4.1 mmol) in anhydrous dimethyl formamide (5 mL) under nitrogen. After stirring for 0.5 h at RT, the reaction mixture was heated for 20 h at 80-95° C. Thereafter, the reaction was cooled to RT, water (30 mL) and ethyl acetate (30 mL) were added, and the organic layer was separated from the aqueous mixture. The organic extract was washed with brine, dried over sodium sulfate and the solvent was evaporated in vacuo. The residue was purified by chromatography using silica gel to afford the title compound as a pale yellow liquid (0.46 g, 75%).

Workup

  1. temperaturethe reaction mixture was heated for 20 h at 80-95° C
  2. temperatureThereafter, the reaction was cooled to RT
  3. customthe organic layer was separated from the aqueous mixture
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-bdfbe09040d94836af576c32d8a12371
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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