4-Pyridinemethanamine → HCID 19081384, compound

HRID 963194Notes

Reaction equation

HRID 963194 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH2:8])=[CH:3][CH:2]=1.[C:9]([C:11]1[C:12](=[O:21])[N:13]([CH2:19][CH3:20])[N:14]=[CH:15][C:16]=1C#N)#[N:10]>C(O)C>[C:9]([C:11]1[C:12](=[O:21])[N:13]([CH2:19][CH3:20])[N:14]=[CH:15][C:16]=1[NH:8][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)#[N:10]

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 19081369HCID 19081369, compound

Product 1

HCID 19081384HCID 19081384, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Into 305 ml of an absolute ethanol solution of 1.9 g of 4-picolylamine, 30 ml of an absolute ethanol suspension of 1.4 g of 4,5-dicyano-2-ethylpyridazin-3-(2H)-one was dropwise added under cooling with ice over a period of 30 minutes. After completion of the dropwise addition, the mixture was reacted at room temperature overnight. Then, ethanol was distilled off under reduced pressure. To the residue, 250 ml of ethyl acetate and 100 ml of water were added, followed by shaking. The ethyl acetate layer was dried over anhydrous sodium sulfate and then distilled under reduced pressure. The residue was subjected to column chromatography, and using an eluent (ethyl acetate:methanol=40:1), 0.3 g of the desired product (Compound No. 47) was obtained.

Workup

  1. additionwas dropwise added
  2. temperatureunder cooling with ice over a period of 30 minutes
  3. additionAfter completion of the dropwise addition
  4. customthe mixture was reacted at room temperature overnight
  5. distillationThen, ethanol was distilled off under reduced pressure
  6. additionTo the residue, 250 ml of ethyl acetate and 100 ml of water were added
  7. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  8. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-518a14050479467cbb702a82a571450c
Source dataset
uspto-grants-1998_06
Patent number
US05763439

Reaction notes

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