Propylamine → HCID 15338359, compound

HRID 1440801Notes

Reaction equation

HRID 1440801 reaction equation
Cl[C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:17]([NH2:20])[CH2:18][CH3:19]>C(O)C>[CH2:17]([NH:20][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 15338358Ethyl 2-chloroquinoline-3-carboxylate

Product 1

HCID 15338359HCID 15338359, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An solution of ethyl 2-chloroquinoline-3-carboxylate (1.1 g) [(K. Shimizu et al., J. Pharm. Soc. Jpn., 87, 672(1967)] and propylamine (1.8 g) in ethanol (20 ml) was heated at 95° C. for 8 hours in a sealed tube. The reaction mixture was concentrated under reduced pressure, to which was added a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with chloroform. The extract was dried over anhydrous sodium sulfate, then the solvent was distilled off. The residue was purified by column chromatography on silica gel to afford the title compound as a yellow oil (0.98 g, 80%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, to which
  2. additionwas added a saturated aqueous solution of sodium hydrogencarbonate
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-01e3ef099ebf4b59890dfde15fcebcca
Source dataset
uspto-grants-1996_03
Patent number
US05500427

Reaction notes

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