Methyl 1-(3-chloropyridin-2-yl)-3-(hydroxymethyl)-1H-pyrazole-5-carboxylate → HCID 86661390, compound

HRID 1630671Notes

Reaction equation

HRID 1630671 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([CH2:17][OH:18])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1>ClCCl.[O-2].[Mn+4].[O-2]>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]([CH:17]=[O:18])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 53235501Methyl 1-(3-chloropyridin-2-yl)-3-(hydroxymethyl)-1H-pyrazole-5-carboxylate

Product 1

HCID 86661390HCID 86661390, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

A little at a time, 3.90 g (44.9 mmol) of manganese(IV) oxide were added to a solution of 3.00 g (11.2 mmol) of methyl 1-(3-chloropyridin-2-yl)-3-(hydroxymethyl)-1H-pyrazole-5-carboxylate in 162 mg of dichloromethane, and the mixture was stirred at 40° C. for 4 hours. After cooling to 20° C., a further 3.90 g (44.9 mmol) of manganese(IV) oxide were added, and the mixture was heated at 40° C. overnight. After cooling to 20° C., the mixture was filtered through Celite and the filtrate was freed from the solvent under reduced pressure.

Workup

  1. temperatureAfter cooling to 20° C.
  2. temperaturethe mixture was heated at 40° C. overnight
  3. temperatureAfter cooling to 20° C.
  4. filtrationthe mixture was filtered through Celite

Sources & evidence

ORD record
ord-f9d2db6d51334751ae56bfb878b266a7
Source dataset
uspto-grants-2014_07
Patent number
US08791139B2

Reaction notes

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