3-Pyridineacetic acid → N-methoxy-N-methyl-2-(pyridin-3-yl)acetamide

HRID 1274393Notes

Reaction equation

HRID 1274393 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([OH:10])=O)[CH:2]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.Cl.[CH3:34][NH:35][O:36][CH3:37]>C(N(CC)CC)C>[CH3:37][O:36][N:35]([CH3:34])[C:8](=[O:10])[CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 1083-Pyridineacetic acidHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 22120669N-methoxy-N-methyl-2-(pyridin-3-yl)acetamideYield 70.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

To a suspension of pyridin-3-yl-acetic acid (856 mg in 20 mL dry methylene chloride) was added in sequence 0.35 mL triethylamine, 1-hydroxybenzotriazole (862 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.08 g) and the reagents allowed to mix for 1 hour. At this time, N,O-dimethylhydroxylamine hydrochloride (1.22 g) was added followed by 2.0 mL triethylamine and the reaction stirred at room temperature. After 20 hours, the mixture applied to a silica gel column and purified by flash chromatography (methylene chloride:methanol, 94:6) to give the title compound (796 mg).

Workup

  1. additionto mix for 1 hour
  2. custompurified by flash chromatography (methylene chloride:methanol, 94:6)

Sources & evidence

ORD record
ord-c25271b7a9c147e59ef5873f02819cb3
Source dataset
uspto-grants-2000_12
Patent number
US06156767

Reaction notes

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