2,4-Dinitrotoluene → 4-[(E)-2-(2,4-dinitrophenyl)ethenyl]pyridine

HRID 900638

Reaction equation

HRID 900638 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH3:13])([O-:3])=[O:2].[N:14]1[CH:19]=[CH:18][C:17]([CH:20]=O)=[CH:16][CH:15]=1.N1CCCC1>>[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1/[CH:13]=[CH:20]/[C:17]1[CH:18]=[CH:19][N:14]=[CH:15][CH:16]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 84612,4-DinitrotolueneHCID 133894-PyridinecarboxaldehydeHCID 31268Pyrrolidine

Product 1

HCID 866035104-[(E)-2-(2,4-dinitrophenyl)ethenyl]pyridine

Procedure

1.4 g (7.7 mmol) of 2,4-dinitrotoluene, 0.82 g (7.7 mmol) of pyridine-4-carboxaldehyde and 0.2 mL of pyrrolidine were charged to a round-bottomed flask. The flask was fitted with a splash protector and then irradiated for 20 seconds in a domestic microwave oven (850 watt). The mixture was then allowed to cool, and the product was caused to precipitate by addition of 20 mL of acetone. Suction-filtration and drying at 40° C. under vacuum have 0.9 g of product (43% of the theoretical).

Workup

  1. customThe flask was fitted with a splash protector
  2. customirradiated for 20 seconds in a domestic microwave oven (850 watt)
  3. temperatureto cool
  4. customto precipitate by addition of 20 mL of acetone
  5. filtrationSuction-filtration
  6. customdrying at 40° C. under vacuum

Sources & evidence

ORD record
ord-1b47debb339e4527b874fe5e5ca4be29
Source dataset
uspto-grants-2008_04
Patent number
US07361198B2

Linked notes

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