2-Methylmorpholine → HCID 13292750, compound

HRID 596277Notes

Reaction equation

HRID 596277 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5](Cl)=[C:4]2[CH:9]=[N:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:12]([CH3:13])[C:3]=12.[CH3:20][CH:21]1[O:26][CH2:25][CH2:24][NH:23][CH2:22]1>>[CH3:13][C:12]1[C:3]2[C:4](=[C:5]([N:23]3[CH2:24][CH2:25][O:26][CH:21]([CH3:20])[CH2:22]3)[N:6]=[N:7][C:2]=2[N:23]2[CH2:24][CH2:25][O:26][CH:21]([CH3:20])[CH2:22]2)[CH:9]=[N:10][C:11]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 4106152-MethylmorpholineHCID 12324663HCID 12324663, compound

Product 1

HCID 13292750HCID 13292750, compound

Procedure

8.00 mg. of 1,4-dichloro-8-methyl-7-phenylpyrido[3,4-d]pyridazine was heated together with 2 g. of 2-methyl-morpholine at 120° C for 1.5 hours, after which time the excess 2-methylmorpholine was distilled off. To the residue was added 30 ml. of water and the resultant crystals were recovered by filtration and purified by column chromatography (silica gel; acetone: benzene=1:8) in the same manner described in Example 3. After removal of the solvent, the residue was dissolved in 20 ml. of ethanol. Following the addition of 2 ml. of water, the solution was concentrated to dryness. To the residue was added 20 ml. of water, followed by stirring. The resultant crystals were dried in a vacuum dryer at 50°-60° C for 12 hours, whereupon 600 mg. of 8-methyl-1,4-bis(2-methylmorpholino)-7-phenylpyrido-[3,4-d]pyridazine was obtained. Melting point: 96°-99° C.

Workup

  1. distillationafter which time the excess 2-methylmorpholine was distilled off
  2. additionTo the residue was added 30 ml
  3. filtrationof water and the resultant crystals were recovered by filtration
  4. custompurified by column chromatography (silica gel; acetone: benzene=1:8) in the same manner
  5. customAfter removal of the solvent
  6. dissolutionthe residue was dissolved in 20 ml
  7. additionthe addition of 2 ml
  8. concentrationof water, the solution was concentrated to dryness
  9. additionTo the residue was added 20 ml
  10. customThe resultant crystals were dried in a vacuum dryer at 50°-60° C for 12 hours, whereupon 600 mg

Sources & evidence

ORD record
ord-2b2c3213a7c44a5d93d5bbbd6b356592
Source dataset
uspto-grants-1977_03
Patent number
US04010265

Reaction notes

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