Malonic Acid → HCID 58248011, compound

HRID 2371064Notes

Reaction equation

HRID 2371064 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)=[C:7]([CH:10]=1)[C:8]#[N:9])=O.C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19].N1CCCCC1>N1C=CC=CC=1>[C:8]([C:7]1[CH:10]=[C:3](/[CH:1]=[CH:17]/[C:18]([OH:20])=[O:19])[CH:4]=[CH:5][C:6]=1[N:11]1[CH:15]=[N:14][CH:13]=[N:12]1)#[N:9]

Participants

5

Reactant 3

HCID 867Malonic AcidHCID 8082PiperidineHCID 59509576HCID 59509576, compound

Product 1

HCID 58248011HCID 58248011, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.05 g (10.3 mmol) of 5-formyl-2-(1H-1,2,4-triazol-1-yl)benzonitrile (lit.: WO-A-2008/019760), 1.60 g (16.6 mmol) of malonic acid and 176 mg (2.07 mmol) of piperidine were stirred in 20 ml of pyridine at 80° C., for 48 hours. The pyridine was distilled off under reduced pressure. The residue was added to ice-water and adjusted to pH 1 with concentrated hydrochloric acid. The aqueous phase was extracted repeatedly with ethyl acetate and dried over sodium sulphate, and the solvent was distilled off under reduced pressure.

Workup

  1. distillationThe pyridine was distilled off under reduced pressure
  2. additionThe residue was added to ice-water
  3. extractionThe aqueous phase was extracted repeatedly with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7cab42ab84c440e7800825c0a394b449
Source dataset
uspto-grants-2014_04
Patent number
US08710242B2

Reaction notes

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