Water → 6-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyloxy]-phenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 465428

Reaction equation

HRID 465428 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:13][CH2:14][C:15](=[O:18])[NH:16][N:17]=2)=[CH:8][CH:7]=1)[C:2]([CH3:4])=O.C(=O)(O)O.[OH:23][CH:24]([C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=1)[CH2:25][NH2:26].O>C1C=CC=CC=1>[Cl:33][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][CH:30]=1)[CH:24]([OH:23])[CH2:25][NH:26][CH:2]([CH3:4])[CH2:1][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH2:13][CH2:14][C:15](=[O:18])[NH:16][N:17]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 144418546-[4-(2-Oxopropoxy)phenyl]-4,5-dihydropyridazin-3(2H)-oneHCID 678659382-(3-Chlorophenyl)-2-hydroxyethylamine carbonate

Product 1

HCID 198744866-[4-[2-[(3-chloro-beta-hydroxyphenethyl)amino]propyloxy]-phenyl]-4,5-dihydro-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4,5-dihydro-6-(4-acetonyloxyphenyl)3(2H)-pyridazinone (0.3 g) and 2-hydroxy-2-(3-chlorophenyl) ethanamine carbonate (0.26 g) in dry benzene (80 ml) was heated under reflux, with azeotropic removal of water, for 3 hr. The solvent was evaporated and the residue dissolved in methanol (80 ml) and treated with sodium cyanoborohydride (0.5 g). After 18 hr. the methanol was evaporated and the residue partitioned between ethylacetate and brine. The organic phase was washed with water, dried (MgSO4) and evaporated to a gum which was chromatographed on silica gel. Elution with methanol-chloroform (4:96) gave 6-[4-[2-[(3-chloro-β-hydroxyphenethyl)amino]propyloxy]-phenyl]-4,5-dihydro-3(2H)-pyridazinone as a white crystalline solid, m.p.t. 140°-158° C., as a 1:1 mixture of diastereoisomers.

Workup

  1. temperaturewas heated
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in methanol (80 ml)
  4. additiontreated with sodium cyanoborohydride (0.5 g)
  5. customthe methanol was evaporated
  6. customthe residue partitioned between ethylacetate and brine
  7. washThe organic phase was washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated to a gum which
  10. customwas chromatographed on silica gel
  11. washElution with methanol-chloroform (4:96)

Sources & evidence

ORD record
ord-a4f3ae6b88ec4b7a9f7bb2a9e9365ace
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Linked notes

Loading…