Isopropyl iodide → HCID 11369056, compound

HRID 1966014Notes

Reaction equation

HRID 1966014 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1.[CH:8]([I:11])([CH3:10])[CH3:9]>C(#N)C>[I-:11].[CH:8]([N+:1]1[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][CH:2]=1)([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 6362Isopropyl iodideHCID 79634-Methylpyridine

Product 1

HCID 11369056HCID 11369056, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 4-picoline (2.5 g, 26.8 mmol) in acetonitrile (50 ml) was added isopropyl iodide (9.1 g, 53.6 mmol) drop wise, the resultant mixture was heated at 90° C. for 24 hours. After cooling the solvent was evaporated to give a red solid which on trituration with ethyl acetate yielded 1-isopropyl-4-methylpyridinium iodide (6.01 g, 85%) as a cream solid, 1H NMR D6-DMSO δ? 1.6 (d, 6H, J=7), 2.6 (s, 3H), 4.95 (m, 1H), 8.0 (d, 2H J=6), 9.05 (d, 2H J=6).

Workup

  1. temperatureAfter cooling the solvent
  2. customwas evaporated
  3. customto give a red solid which on trituration with ethyl acetate

Sources & evidence

ORD record
ord-18a59a21d71c466aa38d732f8eac6b53
Source dataset
uspto-grants-2013_04
Patent number
US08420637B2

Reaction notes

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