Pyridine → HCID 50896777, compound

HRID 1172584Notes

Reaction equation

HRID 1172584 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][C:9]([NH2:11])=O)=[CH:6][C:5]([CH3:12])=[N:4]1)[CH3:2].N1C=CC=CC=1>O1CCOCC1>[CH2:1]([N:3]1[C:7]([CH2:8][C:9]#[N:11])=[CH:6][C:5]([CH3:12])=[N:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 1049PyridineHCID 57659603HCID 57659603, compound

Product 1

HCID 50896777HCID 50896777, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-Ethyl-5-methyl-2H-pyrazol-3-yl)-acetamide (2.0 g, 11.96 mmol) was dissolved in dioxane (180 ml) followed by the addition of pyridine (1.89 g, 23.9 mmol). The resulting solution was cooled to 0° C. and TFM (2.76 g, 13.16 mmol) was added drop by drop. The suspension was then slowly warmed to rt and stirring was continued in total for 4 h. The volatiles were removed under reduced pressure, the residue was dissolved in DCM (150 ml), washed with water (2×100 ml), dried over magnesium sulfate, filtered and concentrated under reduced pressure. After flash-chromatography (silicagel; DCM/methanol=40/1), 1.58 g (88%) of (2-ethyl-5-methyl-2H-pyrazol-3-yl)-acetonitrile was obtained. LC-MS: tR=0.65 min; [M+H]+=150.18.

Workup

  1. additionTFM (2.76 g, 13.16 mmol) was added drop by drop
  2. temperatureThe suspension was then slowly warmed to rt
  3. customThe volatiles were removed under reduced pressure
  4. dissolutionthe residue was dissolved in DCM (150 ml)
  5. washwashed with water (2×100 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ca79fe6421fc4a3b80c91f9fba8ed25c
Source dataset
uspto-grants-2010_11
Patent number
US07834028B2

Reaction notes

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