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

HRID 1774073Notes

Reaction equation

HRID 1774073 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-dc40415d86584e28bfc9add5d0c5c3cf
Source dataset
uspto-grants-2016_02
Patent number
US09255933B2

Reaction notes

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