Water → HCID 21311473, compound

HRID 971983Notes

Reaction equation

HRID 971983 reaction equation
[OH:1][CH:2]([CH2:18][CH3:19])[CH2:3][N:4]1[C:9](=[O:10])[CH2:8][CH2:7][C:6]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[N:5]1.[C:20]1(=[O:26])[O:25][C:23](=[O:24])[CH2:22][CH2:21]1.N1C=CC=CC=1.O>C(Cl)Cl>[C:20]([OH:25])(=[O:26])[CH2:21][CH2:22][C:23]([OH:1])=[O:24].[OH:1][CH:2]([CH2:18][CH3:19])[CH2:3][N:4]1[C:9](=[O:10])[CH2:8][CH2:7][C:6]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[N:5]1.[OH:1][CH:2]([CH2:18][CH3:19])[CH2:3][N:4]1[C:9](=[O:10])[CH2:8][CH2:7][C:6]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[N:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7922Succinic anhydrideHCID 60670738958-82-6

Product 1

HCID 21311473HCID 21311473, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 25 grams (0.089 mol) of 2-(2-hydroxy-butyl)-6-(p-chlorophenyl)-4,5-dihydro-3(2H)-pyridazinone, 25 grams (0.25 mol) of succinic anhydride and 50 milliliters of pyridine are stirred and heated at 90° for 2.5 hours. The mixture is poured into 100 milliliters of water and 100 milliliters of methylene chloride. The organic layer is separated and washed twice with 100 milliliters of water following which it is treated with anhydrous magnesium sulfate and activated charcoal, filtered through celite and concentrated under vacuum. The residue is dissolved in a mixture of ethanol methylene dichloride and concentrated to about 80 milliliters volume. The precipitate formed (11.4 grams of bis-[2-(2-hydroxy-butyl)-6-(p-chlorophenyl)-4,5-dihydro-3(2H)-pyridazinone] succinate; m.p. 142° ) is removed by filtration. The remaining filtrate is concentrated to a syrup (17 grams) and dissolved in 100 milliliters of diethyl ether. The solution is added dropwise to an ice-coated solution of diethylether saturated with dry ammonia gas. The white solid formed is filtered off, washed with diethyl ether and dissolved in CH2Cl2. The solution is filtered and then treated with petroleum ether yielding 6.0 grams of [2-(2-hydroxybutyl)-6-(p-chlorophenyl)-4,5-dihydro-3(2H)-pyridazinone] succinic acid ester (m.p. 90°-93° )

Workup

  1. temperatureheated at 90° for 2.5 hours
  2. customThe organic layer is separated
  3. washwashed twice with 100 milliliters of water following which it
  4. additionis treated with anhydrous magnesium sulfate and activated charcoal
  5. filtrationfiltered through celite
  6. concentrationconcentrated under vacuum
  7. dissolutionThe residue is dissolved in a mixture of ethanol methylene dichloride
  8. concentrationconcentrated to about 80 milliliters volume

Sources & evidence

ORD record
ord-969a9164c9394d2eac193f6e9f0dae10
Source dataset
uspto-grants-1979_07
Patent number
US04162317

Reaction notes

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