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

HRID 474548Notes

Reaction equation

HRID 474548 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=O)[CH:4]=[N:3]1.C(O)(=O)[CH2:10][C:11]([OH:13])=[O:12].N.Cl>N1CCCCC1.O.N1C=CC=CC=1>[CH3:1][N:2]1[CH:6]=[C:5](/[CH:7]=[CH:10]/[C:11]([OH:13])=[O:12])[CH:4]=[N:3]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 5731171-Methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 1529858(2E)-3-(1-methyl-1H-pyrazol-4-yl)prop-2-enoic acidYield 41.8%

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-methyl-1H-pyrazole-4-carbaldehyde (13 g, 118 mmol), malonic acid (12.29 g, 118 mmol), pyridine (65 ml) and piperidine (0.234 ml, 2.361 mmol) was heated to 110° C. under argon for 4 h. After cooling, water (100 ml) was added, followed by aqueous ammonia (12 ml) to obtain a clear solution, which was acidified to pH ˜1 with hydrochloric acid. The precipitate was collected by filtration, washed with water and dried to obtain the title compound (7.5 g, 40.5% yield). LCMS: rt=0.92 min, [M+H+]=153

Workup

  1. temperatureAfter cooling
  2. customto obtain a clear solution, which
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-eaeb4a57583340d0910fb0f8b51f5850
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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