Hydrochloric Acid → 5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3-carboxylic acid

HRID 872479Notes

Reaction equation

HRID 872479 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][C:4]([C:13]([O:15]C)=[O:14])=[CH:3]1.Cl>[OH-].[Na+]>[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:5][C:4]([C:13]([OH:15])=[O:14])=[CH:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2748711methyl 5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3-carboxylate

Product 1

HCID 91673915-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3-carboxylic acidYield 55.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methyl 5-oxo-1-phenyl-2,5-dihydro-1H-pyrazole-3-carboxylate (0.35 g; 1.60 mmol) in 5 ml of 2M NaOH solution was heated at 60° C. for 2 h after which the reaction mixture was made acidic with 1.5 ml of concentrated HCl which caused the product to form a yellow precipitate. Filtering gave 0.18 g of the product. 1H-NMR (400 MHz; d6-DMSO): δ 5.97 (s, 1H), 7.33-7.37 (m, 1H), 7.48-7.52 (m, 2H), 7.74 (m, 2H).

Workup

  1. customto form a yellow precipitate
  2. filtrationFiltering

Sources & evidence

ORD record
ord-7418567edbec4a588aca287db6da9a0b
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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