Hydrochloric Acid → HCID 69205563, compound

HRID 30649Notes

Reaction equation

HRID 30649 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][N:11]=[CH:10][C:9]=2[CH:13]=O)=[CH:4][CH:3]=1.C(O)(=O)[CH2:16][C:17]([OH:19])=[O:18].N1CCCCC1.Cl>O.COCCOCCOC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][N:11]=[CH:10][C:9]=2/[CH:13]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 6054393-(4-Fluorophenyl)-1H-pyrazole-4-carboxaldehyde

Product 1

HCID 69205563HCID 69205563, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8150DiglymeSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-(4-fluorophenyl)-1H-pyrazole-4-carbaldehyde (1.0 g), malonic acid (0.67 g), piperidine (0.54 g) and bis(2-methoxyethyl) ether (10 mL) was stirred at 110° C. for 6 hrs. Water and 1N hydrochloric acid were added to acidify the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give (2E)-3-[5-(4-fluorophenyl)-1H-pyrazol-4-yl]acrylic acid as colorless crystals (0.12 g, yield 10%) from a fraction eluted with hexane-ethyl acetate (1:9, v/v). Recrystallization thereof from acetone-diisopropyl ether gave colorless prism crystals. melting point: 276-277° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f4f084e1255a4786b917ffac8ea4cc1a
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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