Pyridine → 5-phenyl-1H-pyrrole-3-carbonitrile

HRID 2209564Notes

Reaction equation

HRID 2209564 reaction equation
[C:1]1([C:7]2[CH2:11][CH:10]([C:12]#[N:13])[CH2:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1>COCCOC>[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([C:12]#[N:13])[CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 12294966HCID 12294966, compound

Product 1

HCID 100807675-phenyl-1H-pyrrole-3-carbonitrileYield 59.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Under a nitrogen purge 2,3-dichloro-5,6-dicyano-1,4-bonzoquinone (0.23 g; 0.001 mol) and 2-phenyl-1-pyrroline-4-carbonitrile (0.17 g; 0.001 mol) is dissolved in 1,2-dimethoxyethane (13 mL) to form a clear orange solution. Pyridine (0.08 mL; 0,001 mol) is added in a single portion, causing a slight exotherm (to ca. 28° C.) and an immediate formation of a green/grey precipitate. The suspension is stirred at room temperature for 18 hours during which time much of the solvent evaporates. The brownish semi-solid residue is partitioned between ether and a half-saturated solution of sodium carbonate. The red-brown aqueous layer is extracted twice with ether and the combined ether layer is washed with fresh water, then saturated sodium chloride. After drying with MgSO4, solvent is removed under reduced pressure to obtain a white semi-solid. This material was recrystallized from ethylene dichloride (DARCO treatment) to yield lavender crystals (0.1 g).

Workup

  1. customto form a clear orange solution
  2. customa slight exotherm (to ca. 28° C.)
  3. customevaporates
  4. customThe brownish semi-solid residue is partitioned between ether
  5. extractionThe red-brown aqueous layer is extracted twice with ether
  6. washthe combined ether layer is washed with fresh water
  7. dry with materialAfter drying with MgSO4, solvent
  8. customis removed under reduced pressure
  9. customto obtain a white semi-solid
  10. customThis material was recrystallized from ethylene dichloride (DARCO treatment)

Sources & evidence

ORD record
ord-235458f71a2f4b1a808460a5fb75861d
Source dataset
uspto-grants-1995_10
Patent number
US05455263

Reaction notes

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