3,4-Dichlorobenzaldehyde → 4-(3,4-Dichlorophenyl)-1,4,6,7-tetrahydro-2-methyl-3-(methylsulfonyl)-5H-cyclopenta[b]pyridin-5-one

HRID 1386047Notes

Reaction equation

HRID 1386047 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=O.[CH3:11][S:12]([CH2:15][C:16](=O)[CH3:17])(=[O:14])=[O:13].[NH2:19][C:20]1[CH2:24][CH2:23][C:22](=[O:25])[CH:21]=1>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]2[C:15]([S:12]([CH3:11])(=[O:14])=[O:13])=[C:16]([CH3:17])[NH:19][C:20]3[CH2:24][CH2:23][C:22](=[O:25])[C:21]2=3)[CH:7]=[CH:8][C:9]=1[Cl:10]

Participants

5

Reactant 3

HCID 227103,4-DichlorobenzaldehydeHCID 786951-(Methylsulphonyl)acetoneHCID 122914403-Aminocyclopent-2-en-1-one

Product 1

HCID 181872074-(3,4-Dichlorophenyl)-1,4,6,7-tetrahydro-2-methyl-3-(methylsulfonyl)-5H-cyclopenta[b]pyridin-5-oneYield 21.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-Dichlorobenzaldehyde (175 mg, 1.0 mmol), methanesulfonylacetone (137 mg, 1.01 mmol) and 3-aminocyclopentenone (95 mg, 0.98 mmol) were heated to 80° C. in ethanol (4 mL) in a sealed tube for 3 days, cooled and the solvent evaporated. The crude material was flash chromatographed on silica gel (5% methanol/chloroform) to provide 80 mg of the title compound as a tan solid.

Workup

  1. temperaturecooled
  2. customthe solvent evaporated
  3. customchromatographed on silica gel (5% methanol/chloroform)

Sources & evidence

ORD record
ord-777af867ebbe4454b7246eb3bd5885f0
Source dataset
uspto-grants-2001_07
Patent number
US06265417B1

Reaction notes

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