Hydrogen Peroxide → 2,5-Dichloropyridine-4-carbonitrile

HRID 963293Notes

Reaction equation

HRID 963293 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]#[N:9].OO.[Cl:12]C1C=CC=C(C(O[O-])=O)C=1.P(Cl)(Cl)([Cl:25])=O>>[C:8]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([Cl:12])[C:2]=1[Cl:1])#[N:9].[C:8]([C:7]1[C:2]([Cl:1])=[CH:3][N:4]=[C:5]([Cl:25])[CH:6]=1)#[N:9]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 24813Phosphorus oxychlorideHCID 106783063-Chloropyridine-4-carbonitrileHCID 14904487m-Chloroperbenzoate

Product 2

HCID 135602102,5-Dichloropyridine-4-carbonitrileHCID 190820712,3-Dichloropyridine-4-carbonitrile

Procedure

3-chloro-4-cyanopyridine is converted to N-oxide by means of an oxidizing agent such as hydrogen peroxide or m-chloroperbenzoate, and phosphorus oxychloride is reacted thereto to obtain 4-cyano-2,3-dichloropyridine and 4-cyano-2,5-dichloropyridine. These compounds can be separated by column chromatography. The separated compounds are respectively hydrolyzed under an alkaline condition or an acidic condition to obtain the respective carboxylic acids, which are then subjected to Curtius rearrangement and then treated with trifluoroacetic acid to obtain 4-amino-2,3-dichloro-pyridine and 4-amino-2,5-dichloropyridine,

Workup

  1. customis reacted

Sources & evidence

ORD record
ord-bea03edf1f964a9d90110b57046e56da
Source dataset
uspto-grants-1998_06
Patent number
US05763463

Reaction notes

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