Propanal → HCID 23510375, compound

HRID 1883178Notes

Reaction equation

HRID 1883178 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH:11](=O)[CH2:12][CH3:13].N1CCCCC1>C(O)C>[Cl:10][C:8]1[CH:9]=[C:2]2[C:3]([CH:4]=[C:12]([CH3:13])[CH:11]=[N:1]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 527Propanal2×HCID 8082Piperidine2×HCID 112521382-Amino-4-chlorobenzaldehyde

Product 1

HCID 23510375HCID 23510375, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under nitrogen atmosphere, to a solution of 2-amino-4-chloro-benzaldehyde (467 mg) in ethanol (10 mL) were added propanal (250 μL) and piperidine (50 μl), and the mixture was heated under reflux. Further, to the mixture were added propanal (800 μL) and piperidine (250 μL) in several portions, and the mixture was heated under reflux for total 9 hours. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (hexane/ethyl acetate=6/1) to give 7-chloro-3-methylquinoline (401 mg, 75%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for total 9 hours
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column (hexane/ethyl acetate=6/1)

Sources & evidence

ORD record
ord-b2908ce18d594cfa866a87e5c44fe7bd
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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