Hydrochloric Acid → (2E)-3-(4-bromo-1-methyl-1H-pyrazol-3-yl)prop-2-enoic acid

HRID 750791Notes

Reaction equation

HRID 750791 reaction equation
[Br:1][C:2]1[C:3]([CH:8]=O)=[N:4][N:5]([CH3:7])[CH:6]=1.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1.Cl>N1C=CC=CC=1>[Br:1][C:2]1[C:3](/[CH:8]=[CH:11]/[C:12]([OH:14])=[O:13])=[N:4][N:5]([CH3:7])[CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 27355954-bromo-1-methyl-1H-pyrazole-3-carbaldehyde

Product 1

HCID 69268888(2E)-3-(4-bromo-1-methyl-1H-pyrazol-3-yl)prop-2-enoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-bromo-1-methyl-1H-pyrazole-3-carbaldehyde (1.00 g, 5.29 mmol), malonic acid (825 mg, 7.94 mmol) and piperidine (0.12 mL, 1.2 mmol) in pyridine (0.60 mL) was heated to reflux for 3 hours. The mixture was then poured into 10% HCl and extracted with ethyl acetate (3×). The combined extracts were dried (Na2SO4) and concentrated in vacuo to afford (2E)-3-(4-bromo-1-methyl-1H-pyrazol-3-yl)prop-2-enoic acid as a colorless solid.

Workup

  1. temperatureto reflux for 3 hours
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02714de4e897490886a7d2056dca5629
Source dataset
uspto-grants-2008_07
Patent number
US07405229B2

Reaction notes

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