Benzene → 2-(2,2-Dimethyl-5-phenyl-3,4-dihydro-2H-pyrrol-3-yl)pyridine

HRID 1730160Notes

Reaction equation

HRID 1730160 reaction equation
[CH3:1][C:2]1([CH3:11])[C:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:3]1.C([C:14]1C=CC=C[N:15]=1)=C.[CH:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH3:11][C:2]1([CH3:1])[N:3]=[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:5][CH:10]1[C:9]1[CH:8]=[CH:7][CH:6]=[CH:14][N:15]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 75212-VinylpyridineHCID 3082152,2-Dimethyl-3-phenyl-2H-azirene

Product 1

HCID 126213452-(2,2-Dimethyl-5-phenyl-3,4-dihydro-2H-pyrrol-3-yl)pyridine

Procedure

9.5 G. of 2,2-dimethyl-3-phenyl-2H-azirine and 12 g. of freshly distilled 2-vinylpyridine are irradiated in 2 l. of benzene for 7 hours under the conditions given in Example 11. After evaporation of the solvent under reduced pressure, the resulting residue is taken up in 400 ml. of n-pentane and decolorized with active carbon. After 48 hours at -18° C., the crude product which crystallizes is recrystallized from n-pentane/small amount of benzene to yield 2-(5,5-dimethyl-2-phenyl-1-pyrrolin-4-yl)-pyridine (melting point 101°-102° C.).

Workup

  1. customAfter evaporation of the solvent under reduced pressure
  2. customthe crude product which crystallizes
  3. customis recrystallized from n-pentane/small amount of benzene

Sources & evidence

ORD record
ord-3afad422f28a4c5cacc3ec3a09965c60
Source dataset
uspto-grants-1976_11
Patent number
US03991197

Reaction notes

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