Hydrochloric Acid → HCID 22494359, compound

HRID 1260327Notes

Reaction equation

HRID 1260327 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:8]([CH3:17])[N:7]=1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[CH3:17][N:8]1[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:10][C:6]([C:4]([OH:5])=[O:3])=[N:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67299944HCID 67299944, compound

Product 1

HCID 22494359HCID 22494359, compoundYield 138.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1-methyl-5-pyridin-2-yl-1H-pyrazole-3-carboxylic acid ethyl ester (655 mg, 2.8 mmol) at r.t. in ethanol (6 ml) under an argon atmosphere was added 1 N NaOH (5.7 ml) in one portion. The mixture was stirred at r.t. for 5 hrs, neutralized by the addition of 1 N HCl and concentrated to leave a light brown solid. This was triturated in a mixture of Et2O (10 ml) and EtOH (1 ml). The suspension was stirred at r.t. for 2 h. The solids was collected by filtration, washed with Et2O and dried to give the title compound (0.79 g, 100% with 73% purity; impurity: NaCl) as light brown solid. MS: M=204.2 (M+H)+

Workup

  1. concentrationconcentrated
  2. customto leave a light brown solid
  3. customThis was triturated in a mixture of Et2O (10 ml) and EtOH (1 ml)
  4. stirringThe suspension was stirred at r.t. for 2 h
  5. filtrationThe solids was collected by filtration
  6. washwashed with Et2O
  7. customdried

Sources & evidence

ORD record
ord-90173f1d2f364407999c8d8c05b60a28
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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