4-Pyridinemethanamine → HCID 19081411, compound

HRID 963190Notes

Reaction equation

HRID 963190 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][NH2:8])=[CH:3][CH:2]=1.[C:9]([N:13]1[C:18](=[O:19])[C:17]([CH:20]2[O:25][CH:24]([CH3:26])[CH2:23][CH2:22][O:21]2)=[C:16](Cl)[CH:15]=[N:14]1)([CH3:12])([CH3:11])[CH3:10]>C(O)C>[C:9]([N:13]1[C:18](=[O:19])[C:17]([CH:20]2[O:25][CH:24]([CH3:26])[CH2:23][CH2:22][O:21]2)=[C:16]([NH:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:15]=[N:14]1)([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 773174-PyridinemethanamineHCID 19081391HCID 19081391, compound

Product 1

HCID 19081411HCID 19081411, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Into 20 ml of an absolute ethanol solution of 2.7 g of 4-picolylamine, 20 ml of an absolute ethanol solution of 3.4 g of 2-tert-butyl-5-chloro-4-(4-methyl-1,3-dioxan-2-yl)pyridazin-3-(2H)-one was dropwise added at room temperature. The mixture was reacted overnight under heating and refluxing and then left to cool. Ethanol was distilled off under reduced pressure, and then 150 ml of ethyl acetate was added to the residue. The mixture was washed with water and dried over anhydrous sodium sulfate. Then, the solvent was distilled off. The residue was subjected to column chromatography. Using an eluent (ethyl acetate:methanol=30:1 to 12:1), 1.2 g of the desired product (Compound No. 44) having a melting point of from 150° to 153° C. and 0.18 g of amorphous 4-tert-butyl-5-(4-pyridylmethylamino)-4-(4-pyridylmethyliminomethylidenyl)pyridazin-3-(2H) -one (Compound No. 2) as a by-product, were obtained.

Workup

  1. customThe mixture was reacted overnight
  2. temperatureunder heating
  3. temperaturerefluxing
  4. waitleft
  5. temperatureto cool
  6. distillationEthanol was distilled off under reduced pressure
  7. addition150 ml of ethyl acetate was added to the residue
  8. washThe mixture was washed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThen, the solvent was distilled off
  11. customof from 150° to 153° C. and 0.18 g of amorphous 4-tert-butyl-5-(4-pyridylmethylamino)-4-(4-pyridylmethyliminomethylidenyl)pyridazin-3-(2H) -one (Compound No. 2)
  12. customwere obtained

Sources & evidence

ORD record
ord-614231baf7a84e7aa3283d043f8107c5
Source dataset
uspto-grants-1998_06
Patent number
US05763439

Reaction notes

Loading…