Morpholine → 4-Chloro-2-(4-methoxybenzyl)-5-morpholinopyridazin-3(2H)-one

HRID 42707Notes

Reaction equation

HRID 42707 reaction equation
[Cl:1][C:2]1[C:3](=[O:18])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:5]=[CH:6][C:7]=1Cl.[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>O>[Cl:1][C:2]1[C:3](=[O:18])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[N:5]=[CH:6][C:7]=1[N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 165783544,5-Dichloro-2-[(4-methoxyphenyl)methyl]pyridazin-3-one

Product 1

HCID 674464904-Chloro-2-(4-methoxybenzyl)-5-morpholinopyridazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4,5-dichloro-2-(4-methoxybenzyl)pyridazin-3(2H)-one [P. Matyus, Gy. Rabloczky, L. Jaszlits, J. Kosary, M. Kurthy, A. Papp Behr, D. Zara, E. Karpati, A. Kovacs, WO1992/9212137] (10.15 g, 35.61 mmol) and morpholine (7.66 g, 87.92 mmol) in water (200 ml) was refluxed for 18 h. After cooling, the mixture was extracted with dichloromethane (4×40 ml) and the combined extracts were washed with water, dried (Na2SO4) and evaporated. The crude product was purified by recrystallization from ethanol (95%).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with dichloromethane (4×40 ml)
  3. washthe combined extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude product was purified by recrystallization from ethanol (95%)

Sources & evidence

ORD record
ord-c20976d6c90c4bab9a53cd7cd6c747d0
Source dataset
uspto-grants-2013_09
Patent number
US08536210B2

Reaction notes

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