N-Hydroxyacetamidine → 2-Chloro-3-(3-methyl-1,2,4-oxadiazol-5-yl)pyridine

HRID 1455636Notes

Reaction equation

HRID 1455636 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].O[N:12]=[C:13]([NH2:15])[CH3:14]>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([C:4]2[O:5][N:15]=[C:13]([CH3:14])[N:12]=2)=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 30926N-HydroxyacetamidineHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 80272052-Chloro-3-(3-methyl-1,2,4-oxadiazol-5-yl)pyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-chloro nicotinoyl chloride (1.0 eq.) and N′-hydroxy ethanimidamide (1.1 eq) in pyridine (0.6 M) was stirred at 100° C. for 4 h and then concentrated. The residue was purified by flash chromatography (Hexane:EtOAc, 70:30) to afforded the title compound.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography (Hexane:EtOAc, 70:30)

Sources & evidence

ORD record
ord-6f63b64901eb4630b0d7e7d433e36c45
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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