Methanol → 5-(4-Methoxybenzyloxy)-1-methyl-1H-pyrazole-3-carboxylic Acid

HRID 516439Notes

Reaction equation

HRID 516439 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([OH:10])[N:7]([CH3:11])[N:6]=1)=[O:4].CN(C=O)C.C([O-])([O-])=O.[K+].[K+].[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1.CO.[Li+].[OH-].O>>[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][O:10][C:8]2[N:7]([CH3:11])[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:9]=2)=[CH:27][CH:26]=1

Participants

8

Reactant 7

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 178498595HCID 178498595, compound

Product 1

HCID 867051385-(4-Methoxybenzyloxy)-1-methyl-1H-pyrazole-3-carboxylic AcidYield 133.5%

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 5-hydroxy-1-methyl-1H-pyrazole-3-carboxylic acid methyl ester (200 mg, 1 mmol) in DMF (992 μL, 12.8 mmol) at 0° C. was added K2CO3 (195 mg, 1.4 mmol). After 10 minutes at 0° C. p-methoxybenzyl chloride (208 μL, 1.5 mmol) was added, and the resulting mixture was stirred at 60° C. for 1 hour, before allowing to cool to room temperature. MeOH (2.6 mL, 63.2 mmol) was added, followed by LiOH (61.4 mg, 2.6 mmol) in water (2.6 mL, 142 mmol), and the reaction was monitored for completion. The solvent was removed in vacuo. Water was added to the vial and the crude product was acidified with a 1N HCl aqueous solution. The solids were filtered to yield the title compound as a white solid (350 mg).

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent was removed in vacuo
  3. additionWater was added to the vial and the crude product
  4. filtrationThe solids were filtered

Sources & evidence

ORD record
ord-cf357ab4236c474faedb844cdd8ff300
Source dataset
uspto-grants-2015_08
Patent number
US09108934B2

Reaction notes

Loading…