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

HRID 1749247Notes

Reaction equation

HRID 1749247 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(#N)C>[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

4

Reactant 2

HCID 102854-MethylquinolineHCID 123083-Bromo-1-propanol

Product 1

HCID 223147091-(3-Hydroxypropyl)-4-methylquinolinium bromideYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution mixture of lepidine (0.5 g, 3.5 mmol) and 3-bromopropanol (1.9 g, 14 mmol) in acetonitrile (15 mL) was heated to reflux overnight. After cooling to room temperature, the solvent was removed. The resulting mixture was precipitate from methanol and ethyl acetate to give the desired product 7 (0.83 g) in 84% yield. 1H NMR (400 MHz, DMSO-d6) δ 9.41 (d, J=6 Hz, 1H), 8.58 (d, J=8.8 Hz, 1H), 8.54 (dd, J=8.8 Hz, J=1.2 Hz, 1H), 8.26 (td, J=8.0 Hz, J=1.2 Hz, 1H), 8.08-8.03 (m, 2H), 5.09 (t, J=6.8 Hz, 2H), 3.52 (t, J=5.6 Hz, 2H), 3.01 (s, 3H), 2.15-2.08 (m, 2H). 13C NMR (400 MHz, DMSO-d6) δ 158.5, 148.8, 136.8, 135.1, 129.5, 128.9, 127.2, 122.6, 119.3, 57.4, 54.8, 32.0, 19.7.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-0b21f87a7ecc48aeb31f3c45bb46424f
Source dataset
uspto-grants-2015_10
Patent number
US09156814B2

Reaction notes

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