Acetone → 2-(4,5-dihydro-1H-imidazol-2-yl)pyridine

HRID 2118718Notes

Reaction equation

HRID 2118718 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].O.[NH2:10]N.C(Cl)(Cl)Cl.CCC[CH2:19][CH3:20].CC(C)=O>C(O)C>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]1[NH:10][CH2:19][CH2:20][N:2]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 7522Pyridine-2-carbonitrileHCID 24654Hydrazine hydrate (1:1)HCID 19858055HCID 19858055, compound

Product 1

HCID 3457642-(4,5-dihydro-1H-imidazol-2-yl)pyridineYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

8.3 Grams (80 mM) of 2-cyanopyridine was dissolved in 80 ml absolute ethanol and placed in a 250 ml round-bottom flask. 20 Ml of hydrazine hydrate (90%) in 30 ml of ethanol was added to it in one portion and stirred at room temperature for 5 hours. TLC (15:35 chloroform/n-pentane on silica gel) showed no starting material. The reaction mixture was then treated with 25 ml acetone and stirred for 1 hour. It was concentrated to about 100 ml, when a yellow precipitate formed. The latter was washed with water and filtered, to give 9.5 g (65%) yellow crystals. They were dried in vacuo overnight, after which the melting point was 95°-97° C.

Workup

  1. customplaced in a 250 ml round-bottom flask
  2. stirringstirred for 1 hour
  3. concentrationIt was concentrated to about 100 ml, when a yellow precipitate
  4. customformed
  5. washThe latter was washed with water
  6. filtrationfiltered

Sources & evidence

ORD record
ord-f414b16c5b394d8c9675b76389fcf739
Source dataset
uspto-grants-1987_07
Patent number
US04680304

Reaction notes

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