Imidazole → 8-(4-Chlorophenyl)-5,6-dihydroimidazo[1,2-a]pyridine

HRID 1982528Notes

Reaction equation

HRID 1982528 reaction equation
[CH:1]1([C:4]([C:6]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=2)=O)[CH2:3][CH2:2]1.[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>C(Cl)Cl>[Cl:12][C:9]1[CH:8]=[CH:7][C:6]([C:4]2[C:14]3[N:13]([CH:17]=[CH:16][N:15]=3)[CH2:2][CH2:3][CH:1]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 811484-Chlorophenyl cyclopropyl ketone

Product 1

HCID 137640238-(4-Chlorophenyl)-5,6-dihydroimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 25 g (0.14 mol) of 4-chlorophenyl cyclopropyl ketone with 50 g (0.73 mol) of imidazole, and heat to 175° C. for 18 hr. Isolation of the product by column chromatography using 200 g of silica gel and methylene chloride as solvent followed by crystallization from ether affords the title compound.

Workup

  1. customfollowed by crystallization from ether

Sources & evidence

ORD record
ord-740f9eb4f18f4682a5b4335aad01f15f
Source dataset
uspto-grants-1986_06
Patent number
US04596872

Reaction notes

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