Hydrochloric Acid → 1-Methyl-3-propyl-1H-pyrazole-5-carboxylic acid

HRID 2226131Notes

Reaction equation

HRID 2226131 reaction equation
C([O:3][C:4]([C:6]1[N:10]([CH3:11])[N:9]=[C:8]([CH2:12][CH2:13][CH3:14])[CH:7]=1)=[O:5])C.[OH-].[Na+].Cl>O>[CH3:11][N:10]1[C:6]([C:4]([OH:5])=[O:3])=[CH:7][C:8]([CH2:12][CH2:13][CH3:14])=[N:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 101765321H-Pyrazole-5-carboxylic acid, 1-methyl-3-propyl-, ethyl ester

Product 1

HCID 5877971-Methyl-3-propyl-1H-pyrazole-5-carboxylic acidYield 73.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1-Methyl-3-n-propylpyrazole-5-carboxylic acid ethyl ester (20.2 g, 0.10 mol) was suspended in 6N aqueous sodium hydroxide solution (50 ml, 0.30 mol). The mixture was heated to 80° C. for 2 hours then diluted with water (50 ml) and acidified with concentrated hydrochloric acid (25 ml). Filtration gave the carboxylic acid as pale brown crystals (12.3 g, 71%), m.p. 150°-154° C. Found: C, 56.99; H, 7.25; N,16.90. C8H12N2O2 requires C, 57.13; H, 7.19; N, 16.66%.

Workup

  1. filtrationFiltration

Sources & evidence

ORD record
ord-2c44f96e73f5403f9ee27626fd5dc275
Source dataset
uspto-grants-1994_09
Patent number
US05346901

Reaction notes

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