Imidazole → 7-[(1H-imidazol-1yl)phenylmethyl]quinoline

HRID 326264Notes

Reaction equation

HRID 326264 reaction equation
Cl[CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1>CN(C)C=O>[N:19]1([CH:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]2[CH:12]=[C:11]3[C:6]([CH:7]=[CH:8][CH:9]=[N:10]3)=[CH:5][CH:4]=2)[CH:23]=[CH:22][N:21]=[CH:20]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 199671047-(Chlorophenylmethyl)quinoline

Product 1

HCID 199671387-[(1H-imidazol-1yl)phenylmethyl]quinolineYield 33.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3.4 parts of 7-[chlorophenylmethyl]quinoline, 4.5 parts of 1H-imidazole and 72 parts of N,N-dimethylformamide was stirred for 6 hours at 80° C. The reaction mixture was evaporated to dry and the residue was taken up in water. The product was extracted three times with 65 parts of dichloromethane. The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2,2'-oxybispropane and 2-propanone. The product was filtered off and dried, yielding 1.27 parts (33.2%) of 7-[(1H-imidazol-1yl)phenylmethyl]quinoline; mp. 110.7° C. (compound 36).

Workup

  1. customThe reaction mixture was evaporated
  2. customto dry
  3. extractionThe product was extracted three times with 65 parts of dichloromethane
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography over silica gel using
  8. additiona mixture of dichloromethane and methanol (95:5 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from a mixture of 2,2'-oxybispropane and 2-propanone
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-54e7198c9e4e433b8b73a0be1e5690f2
Source dataset
uspto-grants-1993_12
Patent number
US05268380

Reaction notes

Loading…