Hydrochloric Acid → HCID 178516541, compound

HRID 386378

Reaction equation

HRID 386378 reaction equation
[OH:1][C:2]1[N:6]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1C(OCC)=O.[OH-].[K+].Cl>CO>[C:7]1([N:6]2[C:2]([OH:1])=[CH:3][CH:4]=[N:5]2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 178469976HCID 178469976, compound

Product 1

HCID 178516541HCID 178516541, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of ethyl 5-hydroxy-1-(naphthalen-1-yl)-1H-pyrazole-4-carboxylate (480 mg, 1.8 mmol), aqueous potassium hydroxide solution (35%, 2.2 mL, 13.5 mmol) and methanol (5 mL) was heated to reflux for 24 hours. The reaction mixture was then cooled to 0° C., acidified to pH 2 with conc. HCl and refluxed for additional 12 hours to complete decarboxylation. The reaction was then cooled to room temperature and concentrated. The residue was taken up in water and extracted with ethyl acetate, the organic layer washed with water, dried over sodium sulfate and concentrated. Purification by preparative TLC (95% dichloromethane/5% methanol) afforded 1-(naphthalen-1-yl)-1H-pyrazol-5-ol.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. temperaturerefluxed for additional 12 hours
  4. temperatureThe reaction was then cooled to room temperature
  5. concentrationconcentrated
  6. extractionextracted with ethyl acetate
  7. washthe organic layer washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customPurification by preparative TLC (95% dichloromethane/5% methanol)

Sources & evidence

ORD record
ord-a98bd625fd8c4b92bf0a337ae6159102
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Linked notes

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