ethyl 3-chloro-1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazole-5-carboxylate → ethyl 3-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylate

HRID 571001Notes

Reaction equation

HRID 571001 reaction equation
[Cl:1][C:2]1[CH2:6][CH:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1>[O-2].[Mn+4].[O-2].C(#N)C>[Cl:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:4]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:3]=1

Participants

4

Reactant 1

HCID 118021759ethyl 3-chloro-1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazole-5-carboxylate

Product 1

HCID 118022610ethyl 3-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

In a preferred reaction, ethyl 3-chloro-1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazole-5-carboxylate (10b) and acetonitrile are mixed with manganese(IV) oxide and the mixture is heated at about 60° C. until the reaction is completed. The ethyl 3-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylate (10c) is conveniently isolated and purified by standard techniques.

Sources & evidence

ORD record
ord-eaada188888941c2867ad108fb27e9bc
Source dataset
uspto-grants-2015_05
Patent number
US09024031B1

Reaction notes

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