4-Pyridinemethanamine → HCID 19081384, compound

HRID 963193Notes

Reaction equation

HRID 963193 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH2:8])=[CH:3][CH:2]=1.Br[C:10]1[CH:15]=[N:14][N:13]([CH2:16][CH3:17])[C:12](=[O:18])[C:11]=1[C:19]#[N:20]>C(O)C>[C:19]([C:11]1[C:12](=[O:18])[N:13]([CH2:16][CH3:17])[N:14]=[CH:15][C:10]=1[NH:8][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)#[N:20]

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 19081380HCID 19081380, compound

Product 1

HCID 19081384HCID 19081384, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Into 5 ml of an absolute ethanol solution of 0.16 g of 4-picolylamine, 5 ml of an absolute ethanol suspension of 0.11 g of 5-bromo-4-cyano-2-ethylpyridazin-3-(2H)-one, was dropwise added under cooling with ice over a period of 20 minutes. After completion of the dropwise addition, the mixture was reacted at room temperature for one hour. Then, ethanol was distilled off under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed once with water and dried over anhydrous sodium sulfate and then concentrated. To the residue, n-hexane and ethyl ether were added in a small amount for crystallization. The crystals were collected by filtration and dried to obtain 77 mg of the desired product (Compound No. 47) having a melting point of from 193° to 195° C.

Workup

  1. additionwas dropwise added
  2. temperatureunder cooling with ice over a period of 20 minutes
  3. additionAfter completion of the dropwise addition
  4. customthe mixture was reacted at room temperature for one hour
  5. distillationThen, ethanol was distilled off under reduced pressure
  6. extractionthe residue was extracted with ethyl acetate
  7. washThe extract was washed once with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. additionTo the residue, n-hexane and ethyl ether were added in a small amount for crystallization
  11. filtrationThe crystals were collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-49917d35950f489990170d50b6b2f174
Source dataset
uspto-grants-1998_06
Patent number
US05763439

Reaction notes

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