Hydrochloric Acid → 3-chloro-1-methyl-1H-pyrazole-4-carboxylic acid

HRID 1589997Notes

Reaction equation

HRID 1589997 reaction equation
[Cl:1][C:2]1[C:6]([C:7]([O:9]CC)=[O:8])=[CH:5][N:4]([CH3:12])[N:3]=1.[OH-].[Na+].Cl>O>[Cl:1][C:2]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][N:4]([CH3:12])[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13687029Ethyl 3-chloro-1-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 233618493-chloro-1-methyl-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 23.9 g (127 mmol) of ethyl 3-chloro-1-methylpyrazole-4-carboxylate and 10.4 g (260 mmol) of sodium hydroxide in 130 mL of water was prepared and was heated at reflux for 3 hr. The solution that formed was cooled to about 0° C. and neutralized to pH 6.5 with concentrated hydrochloric acid with stirring and the precipitate that formed was recovered by filtration, washed with water, and dried under reduced pressure to obtain 18.1 g (89 percent of theory) of the title compound as a white solid melting at 211°-213° C. (d).

Workup

  1. customwas prepared
  2. temperaturewas heated
  3. temperatureat reflux for 3 hr
  4. customThe solution that formed
  5. customthe precipitate that formed
  6. filtrationwas recovered by filtration
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-a43bcfea1fad456abf591cdcb87617ea
Source dataset
uspto-grants-1993_04
Patent number
US05201938

Reaction notes

Loading…