Triethylamine → N-Methoxy-3-pyridinemethanamine

HRID 249480Notes

Reaction equation

HRID 249480 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Cl)[CH:3]=1.Cl.[CH3:11][O:12][NH2:13].C(N(CC)CC)C>C(#N)C>[CH3:11][O:12][NH:13][CH2:8][C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 22450426N-Methoxy-3-pyridinemethanamineYield 18.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

In 200 ml of acetonitrile was suspended 6.6 g (0.04 mole) of 3-pyridylmethyl chloride hydrochloride, followed by addition of 10 g (0.12 mole) of O-methylhydroxylamine hydrochloride and 16.2 g (0.16 mole) of triethylamine. The mixture was stirred at 50° C. for 15 hours. The insoluble matter was filtered off and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, using EtOH-CHCl3 (1:10) as an eluent. The procedure gave 1.0 g of the title compound as a yellow oil.

Workup

  1. filtrationThe insoluble matter was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ee824a6193404285a9d05abb42499454
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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