4-Methylquinoline → 1-(3-Hydroxypropyl)-4-methylquinolinium bromide

HRID 992905Notes

Reaction equation

HRID 992905 reaction equation
[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1.[Br:12][CH2:13][CH2:14][CH2:15][OH:16].C(O)CCC.O.C(O)(=O)C>O1CCOCC1.CCOCC>[Br-:12].[OH:16][CH2:15][CH2:14][CH2:13][N+:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 102854-MethylquinolineHCID 123083-Bromo-1-propanolHCID 22056973Butanol acetic acid water

Product 1

HCID 223147091-(3-Hydroxypropyl)-4-methylquinolinium bromide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of lepidine (0.49 g, 3.43 mmol) and 3-bromo-1-propanol (3.1 ml, 34 mmol) in 3.0 ml of 1,4-dioxane was refluxed for 17 h. The solution was cooled to room temperature and then diluted with 30 ml of ether. The product separated as an oil and the ether layer was discarded. The oil was crystallized from methylene chloride: 367-mg (38%) yield; TLC (5:3:2, n-butanol/water/acetic acid), Rf=0.40; 1H NMR δ 9.39 (1H, d, J=6.0 Hz, aromatic), 8.57 (2H, t, J=9.1 Hz, aromatic), 8.27 (1H, t, J=7.8 Hz, aromatic), 8.05 (2H, m, aromatic), 5.08 (2H, t, J=7.1 Hz, methylene), 4.81 (1H, t, J=4.9 Hz, hydroxyl), 3.51 (2H, m, methylene), 3.01 (3H, s, 4-methyl), 2.11 (2H, m, methylene). Anal. Calcd. For C13H16BrNO 0.3 H2O; C, 54.29; H, 5.82; N, 4.87. Found C, 53.92; H, 5.43; N, 4.67.

Workup

  1. customThe product separated as an oil
  2. customThe oil was crystallized from methylene chloride
  3. custom367-mg (38%) yield

Sources & evidence

ORD record
ord-a66214beab0f45ed9a18988f9f137f17
Source dataset
uspto-grants-2002_10
Patent number
US06472153B1

Reaction notes

Loading…