Pyridine → 7-Iodo-2-methyl-4-pyrrolidin-1-yl-quinoline

HRID 914925Notes

Reaction equation

HRID 914925 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([I:12])=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.N1C=CC=CC=1.[I-].[K+]>C(O)C>[I:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:3][C:4]([CH3:13])=[N:5]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 4875Potassium IodideHCID 31268PyrrolidineHCID 220545164-Chloro-7-iodo-2-methylquinoline

Product 1

HCID 113366637-Iodo-2-methyl-4-pyrrolidin-1-yl-quinolineYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 2 g of 4-chloro-7-iodo-2-methyl-quinoline (European patent application EP 0497371, CA 143946-47-8) in 20 ml absolute ethanol is treated successively with 1.09 ml pyrrolidine, 0.2 ml pyridine and 50 mg potassium iodide under argon. The resulting mixture is refluxed for 24 h. The solvent is then distilled off. The residue is taken up in 50 ml water and basified to pH 12 with a 2N solution of sodium hydroxyde. The solid is filtered upon precipitation and washed with 20 ml of water and 20 ml of diethylether. The final product is dried under vacuum yielding 1.95 g (87%) of 7-iodo-2-methyl-4-pyrrolidin-1-yl-quinoline as an off-white solid. Mp: 99-102° C. MS (EI): peaks at m/e: 338(M+, 100%), 296 (5%), 183(9%).

Workup

  1. temperatureThe resulting mixture is refluxed for 24 h
  2. distillationThe solvent is then distilled off
  3. filtrationThe solid is filtered upon precipitation
  4. washwashed with 20 ml of water and 20 ml of diethylether
  5. dry with materialThe final product is dried under vacuum

Sources & evidence

ORD record
ord-0b28f60bb2514b28af623454d5e1c84f
Source dataset
uspto-grants-2007_09
Patent number
US07265125B2

Reaction notes

Loading…