Pyridine → 1-(Carbamoylmethyl)pyridinium Chloride

HRID 905597Notes

Reaction equation

HRID 905597 reaction equation
[Cl:1][CH2:2][C:3]([NH2:5])=[O:4].[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(#N)C>[Cl-:1].[NH2:5][C:3](=[O:4])[CH2:2][N+:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 6580Chloroacetamide

Product 1

HCID 27564401-(Carbamoylmethyl)pyridinium ChlorideYield 87.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 2-chloroacetamide (50.00 g, 524.01 mmol) in 100 mL of acetonitrile was added pyridine (41.45 g, 524.01 mmol). After being stirred at 90° C. for 10 h, the suspension was cooled to 22° C., suction-filtered and washed with 100 mL of hexanes. The product, 1-(2-amino-2-oxoethyl)pyridinium chloride (79.10 g, yield: 87%, mp 205.2° C.), was obtained as colorless crystals after being recrystallized from methanol.

Workup

  1. temperaturethe suspension was cooled to 22° C.
  2. filtrationsuction-filtered
  3. washwashed with 100 mL of hexanes

Sources & evidence

ORD record
ord-5f74f9d9571d4912891d0140882c080c
Source dataset
uspto-grants-2011_09
Patent number
US08012965B2

Reaction notes

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