Sodium Methoxide → HCID 14726452, compound

HRID 1087155Notes

Reaction equation

HRID 1087155 reaction equation
Cl[C:2]1[CH:7]=[N:6][N:5]([CH3:8])[C:4](=[O:9])[C:3]=1[NH:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH2:15][CH2:14]1.[CH3:27][O-:28].[Na+]>CO>[CH3:27][O:28][C:2]1[CH:7]=[N:6][N:5]([CH3:8])[C:4](=[O:9])[C:3]=1[NH:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 14726215HCID 14726215, compound

Product 1

HCID 14726452HCID 14726452, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.2 g (0.011 mol) of 5-chloro-2-methyl-4-((2-(4-(2-methoxyphenyl)-1-piperazinyl)ethyl)amino)-3(2H)-pyridazinone are heated in methanol, in which 0.010 mol of sodium methylate is dissolved, under reflux for 50 hours and then concentrated in vacuo. The residue is taken up in water, when 1.6 g of 5-methoxy-2-methyl-4-((2-(4-(2-methoxyphenyl)-1-piperazinyl)ethyl)amino)-3(2H)-pyridazinone (38.9% of theory) precipitate out. The solid is filtered off with suction, dried, dissolved in acetone and converted by addition of fumaric acid at the reflux temperature into 1.50 g (24.5% of theory) of fumarate, m.p. 144°-148° C.; C 54.0%, H 6.1%, N 12.5%, O 27.4%, UV in 0.1N H

Workup

  1. dissolutionis dissolved
  2. temperatureunder reflux for 50 hours
  3. concentrationconcentrated in vacuo
  4. customwhen 1.6 g of 5-methoxy-2-methyl-4-((2-(4-(2-methoxyphenyl)-1-piperazinyl)ethyl)amino)-3(2H)-pyridazinone (38.9% of theory) precipitate out
  5. filtrationThe solid is filtered off with suction
  6. customdried
  7. dissolutiondissolved in acetone
  8. additionconverted by addition of fumaric acid at the reflux temperature into 1.50 g (24.5% of theory) of fumarate, m.p. 144°-148° C.

Sources & evidence

ORD record
ord-728d959aeeb947e19673157e24acdc63
Source dataset
uspto-grants-1991_07
Patent number
US05034391

Reaction notes

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