Ethyl Bromide → 1-Ethyl-4-methylquinolinium bromide

HRID 1774072Notes

Reaction equation

HRID 1774072 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][CH3:14]>C(#N)C>[Br-:12].[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)[CH3:14]

Participants

4

Reactant 2

HCID 6332Ethyl BromideHCID 102854-Methylquinoline

Product 1

HCID 177735061-Ethyl-4-methylquinolinium bromideYield 92%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution mixture of lepidine (0.5 g, 3.5 mmol) and bromoethane (1.96 g, 18 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 6 (0.81 g) in 92% yield. 1H NMR (400 MHz, DMSO-d6) δ 9.44 (d, J=6 Hz, 1H), 8.60 (d, J=9.2 Hz, 1H), 8.54 (dd, J=8.4 Hz, J=1.2 Hz, 1H), 8.26 (td, J=8.0 Hz, J=1.6 Hz, 1H), 8.09-8.04 (m, 2H), 5.06 (tr, J=7.2 Hz, 2H), 3.00 (s, 3H), 1.58 (t, J=7.2 Hz, 3H). 13C NMR (400 MHz, DMSO-d6) δ 158.4, 148.2, 136.6, 135.1, 129.6, 128.9, 127.2, 122.8, 119.2, 52.5, 19.7, 15.2.

Workup

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

Sources & evidence

ORD record
ord-fde13a0c863d435bac580d00cdc3c0fa
Source dataset
uspto-grants-2016_02
Patent number
US09255933B2

Reaction notes

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