Hydrochloric Acid → 3-(Ammoniomethyl)-1-methylpyridin-1-ium chloride

HRID 708341Notes

Reaction equation

HRID 708341 reaction equation
[I-].C([NH:5][CH2:6][C:7]1[CH:8]=[N+:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)(=O)C.[ClH:14]>>[Cl-:14].[NH3+:5][CH2:6][C:7]1[CH:8]=[N+:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1.[Cl-:14]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 1183802663-(Acetamidomethyl)-1-methylpyridin-1-ium iodide

Product 1

HCID 1183799383-(Ammoniomethyl)-1-methylpyridin-1-ium chlorideYield 49%

Conditions

Temperature
100 °C

Procedure

A suspension of 3-(acetamidomethyl)-1-methylpyridin-1-ium iodide (26.9 g, 92 mmol) in HCl (6N, 307 mL, 1.84 mol) was heated to 100° C. for 3 h. The solution was concentrated under reduced pressure (bath temp 80° C.). The resulting red oil solidified overnight and was triturated with MeOH and filtered to afford the title compound (8.76 g, 49%) as an off white solid. The filtrate was concentrated to a red oil, which after standing for 4 days, the formed solid was collected and washed with cold MeOH, affording a second crop (6.5 g, 36%). LCMS: Rt=0.11 min, m/z=123.0 (M+) Method 2m_acidic. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.18 (s, 1H) 9.03 (d, J=6.0 Hz, 1H) 8.66 (d, J=8.1 Hz, 1H) 8.45 (brs, 3H) 8.24 (t, J=7.0 Hz, 1H) 4.38 (s, 3H) 4.30 (s, 2H).

Workup

  1. concentrationThe solution was concentrated under reduced pressure (bath temp 80° C.)
  2. customwas triturated with MeOH
  3. filtrationfiltered

Sources & evidence

ORD record
ord-035b77c5ea9b4a9b8548ac026c6f2941
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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