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

HRID 1374749Notes

Reaction equation

HRID 1374749 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 4-chloro-7-iodo-2-methylquinoline (EP497371, 2.00 g, 6.59 mmol) in ethanol (20 mL) was treated sucessively with pyrrolidine (1.28 g, 18.0 mmol), pyridine (0.2 mL) and potassium iodide (50 mg, 0.30 mmol), 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 afford the title compound (1.95 g, 87%). 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

Sources & evidence

ORD record
ord-fd9d33f4e42347be987cf3552f55a5c0
Source dataset
uspto-grants-2007_01
Patent number
US07166589B2

Reaction notes

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