5-(Aminomethyl)-2-chloropyridine → HCID 86747769, compound

HRID 1464265Notes

Reaction equation

HRID 1464265 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][N:3]=1.[N+:10]([CH2:13][C:14](=O)[CH2:15][CH3:16])([O-:12])=[O:11]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:14]([CH2:15][CH3:16])=[CH:13][N+:10]([O-:12])=[O:11])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 70209275-(Aminomethyl)-2-chloropyridineHCID 132625841-Nitrobutan-2-one

Product 1

HCID 86747769HCID 86747769, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

In 50 ml of toluene, 4.2 g of 2-chloro-5-pyridylmethylamine, 3.5 g of 1-nitro-2-butanone and 0.1 g of p-toluene sulfonic acid were mixed and the mixture was refluxed for 2 hours. The solvent was then distilled off and the residue was purified by column chromatography on silica gel to afford 4.1 g of compound No. 368. m.p. 95°-98° C.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. distillationThe solvent was then distilled off
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3a6b1c6401e64b97965e119a537b4590
Source dataset
uspto-grants-1994_04
Patent number
US05304566

Reaction notes

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