Pyridine → HCID 22641330, compound

HRID 2415482Notes

Reaction equation

HRID 2415482 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([CH3:14])[CH:6]=[C:5]2[Cl:15].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.N1C=CC=CC=1.[Na+].[I-]>CCO>[ClH:15].[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[N:8]=[C:7]([CH3:14])[CH:6]=[C:5]2[N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 5238Sodium IodideHCID 31268PyrrolidineHCID 22641470HCID 22641470, compound

Product 1

HCID 22641330HCID 22641330, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 1 g (3.5 mmol) of 6-bromo-4-chloro-7-methoxy-2-methyl-quinoline in 20 ml of EtOH was treated sequentially at RT and under stirring with 0.49 g (7 mmol) of pyrrolidine, 0.137 g (1.4 mmol) of pyridine and a catalytic amount of NaI. The mixture was then heated to reflux for 20 h, cooled to RT and concentrated in vacuo. The residue was applied to a silica gel column with CH2Cl2/MeOH (7:1) as eluent. Combinations of the purified fractions and concentration in vacuo gave 0.85 g (68.2%) of the 6-bromo-7-methoxy-2-methyl-4-pyrrolidin-1-yl-quinoline hydrochloride as light brown solid. ISP mass spectrum, m/e: 323.3 (M+1 calculated for C15H17BrN2O: 323).

Workup

  1. additionwas treated sequentially at RT
  2. temperatureThe mixture was then heated
  3. temperatureto reflux for 20 h
  4. concentrationconcentrated in vacuo
  5. concentrationCombinations of the purified fractions and concentration in vacuo

Sources & evidence

ORD record
ord-392b3aeca1a844c5a1a359c33937df6d
Source dataset
uspto-grants-2004_11
Patent number
US06818767B2

Reaction notes

Loading…