Hydrochloric Acid → 3-(2-(dimethylamino)ethoxy)-1-methyl-1H-pyrazole-5-carboxylic acid

HRID 577735

Reaction equation

HRID 577735 reaction equation
[OH-].[K+].[CH3:3][N:4]([CH3:19])[CH2:5][CH2:6][O:7][C:8]1[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[N:10]([CH3:18])[N:9]=1.Cl>CCO>[CH3:3][N:4]([CH3:19])[CH2:5][CH2:6][O:7][C:8]1[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[N:10]([CH3:18])[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 86679667ethyl 3-(2-(dimethylamino)ethoxy)-1-methyl-1H-pyrazole-5-carboxylate

Product 1

HCID 866796683-(2-(dimethylamino)ethoxy)-1-methyl-1H-pyrazole-5-carboxylic acidYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

KOH (2.09 g, 37.4 mmol) was dissolved into EtOH (30 mL) and to this solution was added ethyl 3-(2-(dimethylamino)ethoxy)-1-methyl-1H-pyrazole-5-carboxylate (4.5 g, 18.7 mmol) and the mixture stirred at rt overnight. To the reaction mixture was added concentrated HCl (3.1 mL) with stirring and the resulting suspension was filtered and the cake was washed with EtOH (two×20 mL). The filtrate was concentrated to give the title compound (3.3 g, 83% yield) as a brown gum.

Workup

  1. stirringwith stirring
  2. filtrationthe resulting suspension was filtered
  3. washthe cake was washed with EtOH (two×20 mL)
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4cbb75141e2b445bbc33bf5a0397755d
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Linked notes

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