Hydrochloric Acid → HCID 58386165, compound

HRID 1963024Notes

Reaction equation

HRID 1963024 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[C:10]([CH2:18][OH:19])=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[C:10]([CH2:18][OH:19])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58386143HCID 58386143, compound

Product 1

HCID 58386165HCID 58386165, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 1-(4-chlorophenyl)-3-(hydroxymethyl)-1H-pyrazole-4-carboxylate (Example 1D, 1.5 g, 5.34 mmol), sodium hydroxide (0.388 g, 9.70 mmol) and H2O (50 mL) was heated at reflux for 2 h. After cooled down to room temperature, the reaction mixture was acidified with conc. HCl to pH about 5. The solid was collected via filtration, dried under vacuum to give the desired product as white solid (1.22 g, 90% yield). 1H NMR (DMSO-d6) δ 4.68 (s, 2H), 7.54-7.59 (m, 2H), 7.92-7.94 (m, 2H), 8.95 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationThe solid was collected via filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-7d2eec885bf440a7b4d3145775fa5116
Source dataset
uspto-grants-2013_04
Patent number
US08415386B2

Reaction notes

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