4-Methylquinoline → HCID 66588616, compound

HRID 1092749Notes

Reaction equation

HRID 1092749 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Br-:12].[Br:13][CH2:14][CH2:15][CH2:16][N+:17]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:18][CH3:19]>C(#N)C>[Br-:13].[Br-:12].[CH2:18]([N+:17]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:16][CH2:15][CH2:14][N+:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([CH3:1])=[CH:3][CH:4]=1)[CH3:19]

Participants

4

Reactant 2

HCID 102854-MethylquinolineHCID 135522003-Bromo-N,N,N-triethylpropan-1-aminium bromide

Product 1

HCID 66588616HCID 66588616, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Methylquinoline (470 mg, 3.3 mmol), (3-bromopropyl)triethylammonium bromide (1.0 g, 3.3 mmol), and 10 mL acetonitrile were stirred at 90° C. in a pressure vessel for 64 h. After cooling down, the solvent was removed under vacuum and the residue was purified by column chromatography (SiO2, gradient from CH2Cl2 to MeOH) to furnish 1-(3-triethylammoniopropyl)-4-methylquinolinium dibromide as a white solid (1.29 g, 88%). 1H NMR (400 MHz, CD3OD): δ 1.35 (t, J=7.4 Hz, 9 H), 2.54 (m, 2 H), 3.10 (s, 3 H), 3.39 (q, J=7.2 Hz, 6 H), 3.60 (t, J=8.0 Hz, 2 H), 5.18 (t, J=8.0 Hz, 2 H), 8.04 (d, J=6.0 Hz, 1 H), 8.09 (t, 1 H), 8.33 (t, 1 H), 8.61 (d, 1 H), 8.65 (d, 1 H), 9.43 (d, J=6.0 Hz, 1 H); HRMS (FAB+): m/z=365.1581 [M-Br]+ (calcd for C19H30BrN2: 365.1587).

Workup

  1. temperatureAfter cooling down
  2. customthe solvent was removed under vacuum
  3. customthe residue was purified by column chromatography (SiO2, gradient from CH2Cl2 to MeOH)

Sources & evidence

ORD record
ord-1e41eda67a074e48be8ccf4e89946bce
Source dataset
uspto-grants-2012_03
Patent number
US08129532B2

Reaction notes

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