Potassium Carbonate → 2-[(Cyclopentylmethyl)(ethyl)amino]quinoline-3-carbaldehyde

HRID 577778Notes

Reaction equation

Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:20]1(N(C)CC)[CH2:24][CH2:23][CH2:22][CH2:21]1>CN(C)C=O>[CH:20]1([CH2:4][N:3]([CH2:2][CH3:11])[C:2]2[C:11]([CH:12]=[O:13])=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

Conditions

Temperature: 30 °C

Procedure

2-Chloroquinoline-3-carbaldehyde (0.27 grams, 1.40 mmol) and potassium carbonate (0.579 grams, 1.4 mmol) were added to a 25 mL two-necked round bottomed flask. To this flask was added 3 mL of N,N-dimethylformamide (DMF), followed by the drop-wise addition of a dimethylformamide solution of cyclopentyl methyl ethyl amine (0.214 grams, 1.69 mmol). The resulting mixture was refluxed for 2 hours and then cooled to 25-35° C., after which the mixture was poured onto crushed ice (10 mL), and extracted with ethyl acetate (3×50 mL). The organic layer was washed with brine and dried over sodium sulfate. The solvent was evaporated in vacuo to provide the product as a yellow oil. Yield: 0.355 g (89%);

Workup

temperatureThe resulting mixture was refluxed for 2 hours
additionafter which the mixture was poured
extractionextracted with ethyl acetate (3×50 mL)
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-df996184112741b1ae68d1f96dd3bff2
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040558B2

Reaction notes

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