3-Nitrobenzaldehyde → 5-Acetyl-1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine

HRID 247118Notes

Reaction equation

HRID 247118 reaction equation
[CH2:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10][Cl:11])[N:6]=1)[C:2]([CH3:4])=O.[N+:12]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)([O-:14])=[O:13].[NH2:23][C:24](=[CH:26][C:27](=[O:29])[CH3:28])[CH3:25]>C(O)(C)C>[C:27]([C:26]1[CH:18]([C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[C:1]([C:5]2[O:9][N:8]=[C:7]([CH2:10][Cl:11])[N:6]=2)=[C:2]([CH3:4])[NH:23][C:24]=1[CH3:25])(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 1368734-Amino-3-penten-2-oneHCID 138247055-Acetonyl-3-chloromethyl-1,2,4-oxadiazole

Product 1

HCID 1358334235-Acetyl-1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridineYield 67.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred solution of 0.53 g of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole, 0.46 g of 3-nitrobenzaldehyde and 0.30 g of 2-amino-4-oxo-2-pentene in 4 ml of isopropyl alcohol was heated under reflux for 14 hours. The reaction mixture was concentrated in vacuo and the residue was chromatographed on silica gel using benzene-acetonitrile (15:1) as eluent to give 0.79 g of 5-acetyl-1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine.

Workup

  1. temperatureunder reflux for 14 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-3a3cdfe57e434f88a507f35d90df3dfe
Source dataset
uspto-grants-1987_11
Patent number
US04705786

Reaction notes

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