1-Iodopropane → HCID 67317679, compound

HRID 1014173Notes

Reaction equation

HRID 1014173 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH2:17]([I:20])[CH2:18][CH3:19]>CC(=O)C(C)(C)C>[I-:20].[CH3:1][C:2]1[CH:3]=[C:4]([C:11]2[CH:12]=[N+:13]([CH2:17][CH2:18][CH3:19])[CH:14]=[CH:15][CH:16]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 336431-IodopropaneHCID 21071594HCID 21071594, compound

Product 1

HCID 67317679HCID 67317679, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6416PinacoloneSolvent

Conditions

Temperature
102 °C

Procedure

To pinacolone (200 mL, Aldrich) were added 3-(3-methyl-4-nitrophenyl)pyridine (5.3 g, 24.0 mmol) and propyliodide (17.0 g, 100.0 mmol, Fluka). The reaction was stirred at 102° C. for 12 h. Solids were collected and washed with MeOH (2×20 mL) to afford 3-(3-methyl-4-nitrophenyl)-1-propylpyridinium iodide (8.7 g, 90% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.92 (t, J=7.3 Hz, 3 H), 1.97-2.06 (m, 2 H), 2.62 (s, 3 H), 4.62 (t, J=7.3 Hz, 2 H), 7.98 (dd, J=8.5, 1.9 Hz, 1 H), 8.07 (d, J=1.1 Hz, 1H), 8.21 (d, J=8.6 Hz, 1 H), 8.29 (dd, J=8.1, 6.1 Hz, 1 H), 9.00 (d, J=8.4 Hz, 1 H), 9.12 (d, J=6.0 Hz, 1 H), 9.57 (s, 1 H); ESIMS (M+H)+=257.

Workup

  1. customSolids were collected
  2. washwashed with MeOH (2×20 mL)

Sources & evidence

ORD record
ord-5234f914f1234880984302b9976dd130
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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