Triethylamine → 2-Cyano-4-[1-(3-methylphenyl)-3-methyl-1h-pyrazol-5-yl]pyridine

HRID 1635502Notes

Reaction equation

HRID 1635502 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][N:15]=1)[CH2:6][C:7](=O)[CH2:8][C:9](=O)C)#[N:2].Cl.[CH3:17][C:18]1[CH:19]=[C:20]([NH:24][NH2:25])[CH:21]=[CH:22][CH:23]=1.C(N(CC)CC)C>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:6]2[N:24]([C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([CH3:17])[CH:19]=3)[N:25]=[C:8]([CH3:9])[CH:7]=2)[CH:13]=[CH:14][N:15]=1)#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 71562m-Tolylhydrazinium(1+) chlorideHCID 544384121-(2-Cyanoisonicotinyl)-1,3-butanedione

Product 1

HCID 99036362-Cyano-4-[1-(3-methylphenyl)-3-methyl-1h-pyrazol-5-yl]pyridineYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-(2-cyanoisonicotinyl)-1,3-butanedione (1.10 g, 0.0058 mol) and 3-methylphenylhydrazine hydrochloride (0.97 g, 0.0061 mol) in 20 mL of ethanol was added triethylamine (0.85 mL, 0.0061 mol) dropwise. The reaction mixture was heated at reflux overnight (about eighteen hours). The solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude product was purified by chromatography on silica gel (ethyl acetate/hexane, 2:8) to give 1.30 g (87% yield) of product as a yellow solid: mp: 128-130° C.; Anal. Calc'd. for C17H14N4: C, 74.43; H, 5.14; N, 20.42. Found: C, 74.53; H, 5.22; N, 20.29.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight (about eighteen hours)
  3. customThe solvent was removed
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe crude product was purified by chromatography on silica gel (ethyl acetate/hexane, 2:8)

Sources & evidence

ORD record
ord-74588d0bc7d14b129b4158508cda49ec
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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