HCID 86692552, compound → HCID 86692551, compound

HRID 1748599Notes

Reaction equation

HRID 1748599 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([N+:19]([O-])=O)=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]>C(O)C.C(O)(=O)C.[C].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([NH2:19])=[CH:14][N:13]=2)[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 86692552HCID 86692552, compound

Product 1

HCID 86692551HCID 86692551, compoundYield 91.5%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 5-methyl-1-(4-methyl-5-nitropyridin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (22.3 g) in ethanol (600 ml) and acetic acid (50 ml) was added palladium carbon (1.0 g), and stirred at room temperature for 6 hours under hydrogen atmosphere (1 atm). After completion of the reaction, the mixture was filtered through Celite, then the filtrate was concentrated, and the obtained residue was dissolved in chloroform. The organic layer was washed with saturated sodium bicarbonate water and water sequentially, dried over anhydrous sodium sulfate, and then the solvent was evaporated. To the obtained residue was added a small amount of diethyl ether and n-hexane, the precipitated solid was collected by filtration, and heat-dried in vacuo at 60° C. to give 1-(5-amino-4-methylpyridin-2-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (18.3 g) as a pale yellow solid.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated
  4. dissolutionthe obtained residue was dissolved in chloroform
  5. washThe organic layer was washed with saturated sodium bicarbonate water and water sequentially
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. additionTo the obtained residue was added a small amount of diethyl ether and n-hexane
  9. filtrationthe precipitated solid was collected by filtration
  10. customheat-dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-75a0bae18a244818b470373436cbf193
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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