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

HRID 2121635Notes

Reaction equation

HRID 2121635 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>C(O)C.[I-].[K+]>[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 3

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

Product 1

HCID 113366637-Iodo-2-methyl-4-pyrrolidin-1-yl-quinolineYield 87.5%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2 g (6.59 mmol) of 4-chloro-7-iodo-2-methylquinoline (EP497371) in ethanol (20 ml) was treated successively with 1.28 g (18.0 mmol) of pyrrolidine, pyridine (0.2 ml) and 50 mg (0.3 mmol) of potassium iodide and the resulting mixture was refluxed for 24 h. After concentration in vacuo, the residue was taken up in water (50 ml) and basified to pH 12 by addition of 2 M aq. sodium hydroxide solution. The precipitate was collected by filtration, washed with water (20 ml) and ether (20 ml) and dried to in a high vacuum to afford 1.95 g (87%) of 7-iodo-2-methyl-4-pyrrolidin-1-yl-quinoline as off-white solid, m.p. 99-102° C.

Workup

  1. temperaturethe resulting mixture was refluxed for 24 h
  2. concentrationAfter concentration in vacuo
  3. additionbasified to pH 12 by addition of 2 M aq. sodium hydroxide solution
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water (20 ml) and ether (20 ml)
  6. customdried to in a high vacuum

Sources & evidence

ORD record
ord-6a45fa97e63a4f079b87e89a9e8feb5b
Source dataset
uspto-grants-2004_02
Patent number
US06696467B2

Reaction notes

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