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

HRID 1477337Notes

Reaction equation

HRID 1477337 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-c1743ebba7474648b774cd0a6435f09b
Source dataset
uspto-grants-2016_08
Patent number
US09403794B2

Reaction notes

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