Methyl iodide → 3-(Acetamidomethyl)-1-methylpyridin-1-ium iodide

HRID 708340Notes

Reaction equation

HRID 708340 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH:8][C:9](=[O:11])[CH3:10])[CH:2]=1.[CH3:12][I:13]>C(Cl)Cl>[I-:13].[C:9]([NH:8][CH2:7][C:3]1[CH:2]=[N+:1]([CH3:12])[CH:6]=[CH:5][CH:4]=1)(=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 27352253-(Acetamidomethyl)pyridine

Product 1

HCID 1183802663-(Acetamidomethyl)-1-methylpyridin-1-ium iodide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(pyridin-3-ylmethyl)acetamide (13.89 g, 92 mmol) in DCM at 0° C. was added methyl iodide (8.10 mL, 129 mmol). The cooling bath was removed after 10 min and the solution was stirred at rt for 19 h, whereupon it was concentrated in vacuo and used as crude in step 3. LCMS: Rt=0.18 min, m/z=164.9 (M+) Method 2m_acidic. 1H NMR (400 MHz, DMSO-d6) δ 8.91-8.87 (m, 2H) 8.58 (brs, 1H) 8.42 (d, J=8.0 Hz, 1H) 8.09 (t, J=7.0 Hz, 1H) 4.43 (d, J=5.9 Hz, 2H) 4.35 (s, 3H) 1.92 (s, 3H).

Workup

  1. customThe cooling bath was removed after 10 min
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-c6b3d32a3a0a405e88ed05dd0cd1af89
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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