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

HRID 966461Notes

Reaction equation

HRID 966461 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 (211, 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 0.3H2O; 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-85b37fadc841408fa073ae0cb7fcfa5b
Source dataset
uspto-grants-2005_10
Patent number
US06951930B2

Reaction notes

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