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

HRID 247113Notes

Reaction equation

HRID 247113 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](/[CH3:30])=[CH:25]\[C:26]([O:28][CH3:29])=[O:27]>C(O)(C)C>[CH3:4][C:2]1[NH:23][C:24]([CH3:30])=[C:25]([C:26]([O:28][CH3:29])=[O:27])[CH:18]([C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=2)[C:1]=1[C:5]1[O:9][N:8]=[C:7]([CH2:10][Cl:11])[N:6]=1

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 138247055-Acetonyl-3-chloromethyl-1,2,4-oxadiazole

Product 1

HCID 135833416Methyl 1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine-5-carboxylateYield 63.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 8.0 g of 5-acetonyl-3-chloromethyl-1,2,4-oxadiazole, 6.92 g of 3-nitrobenzaldehyde and 5.27 g of methyl 3-aminocrotonate in 20 ml of isopropyl alcohol was heated under reflux for 6 hours. After ice-cooling, the precipitated solid was collected by filtration, washed with cold isopropyl alcohol and dried to give 11.8 g of methyl 1,4-dihydro-2,6-dimethyl-3-(3-chloromethyl-1,2,4-oxadiazol-5-yl)-4-(3-nitrophenyl)pyridine-5-carboxylate as yellow crystals, m.p. 200.5°-201.5° C.

Workup

  1. temperatureunder reflux for 6 hours
  2. temperatureAfter ice-cooling
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with cold isopropyl alcohol
  5. customdried

Sources & evidence

ORD record
ord-9cb3060ce6c548bf914909ad65d20b68
Source dataset
uspto-grants-1987_11
Patent number
US04705786

Reaction notes

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