Potassium Carbonate → 2-(Bis(cyclopropylmethyl)amino)-8-methylquinoline-3-carbaldehyde

HRID 1911754Notes

Reaction equation

HRID 1911754 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:21]1([CH2:24][NH:25][CH2:26][CH:27]2[CH2:29][CH2:28]2)[CH2:23][CH2:22]1>CN(C=O)C>[CH:21]1([CH2:24][N:25]([CH2:26][CH:27]2[CH2:29][CH2:28]2)[C:2]2[C:11]([CH:12]=[O:13])=[CH:10][C:9]3[C:4](=[C:5]([CH3:14])[CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6890822-Chloro-8-methylquinoline-3-carboxaldehydeHCID 15284719Bis(cyclopropylmethyl)amine

Product 1

HCID 574868222-(Bis(cyclopropylmethyl)amino)-8-methylquinoline-3-carbaldehydeYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-8-methyl-quinoline-3-carbaldehyde (0.115 g, 0.559 mmol), and potassium carbonate (0.231 g, 1.67 mmol) were put in a 25 mL two necked RB flask. To this, 3 mL of DMF was added followed by dropwise addition of bis-cyclopropylmethyl amine (0.083 g, 0.67 mmol). The reaction mixture was refluxed for 2 h and was cooled to RT. It was then poured on crushed ice (10 mL) and extracted with EtOAc (3×10 mL). The organic layer was washed with brine and dried over sodium sulphate. The solvent was evaporated under vacuum to give a yellow colored oil (0.081 g, 50%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. additionIt was then poured
  3. extractionextracted with EtOAc (3×10 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulphate
  6. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-8d3f367202de478c9a7e39c50da21180
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

Loading…