Sodium Hydroxide → HCID 70045569, compound

HRID 1761396Notes

Reaction equation

HRID 1761396 reaction equation
Cl.[O:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH:3]1[N:12]([CH3:24])[CH2:13][CH2:14][CH2:15][N:16]1[C:21](=[O:22])[CH:20]=[CH:19][C:18]([Cl:23])=[N:17]1.[OH-].[Na+].[H][H]>[Pd].C(O)C>[ClH:23].[O:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH:3]1[N:12]([CH3:24])[CH2:13][CH2:14][CH2:15][N:16]1[C:21](=[O:22])[CH:20]=[CH:19][CH:18]=[N:17]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 70043172HCID 70043172, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70045569HCID 70045569, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution containing 30 g (0.08 mole) of 2-[3-(benzo[1,4]dioxan-2-yl-methylamino)-1-propyl]-6-chloro-3(2H)-pyridazinone hydrochloride (prepared as described in Example 2), 600 ml of absolute ethanol and 6.2 g of powdered sodium hydroxide is hydrogenated in the presence of 3 g of 5% palladium-on-charcoal catalyst under atmospheric pressure and at room temperature. After ceasing of the hydrogen uptake, the catalyst is filtered off, washed 3 times with 20 ml of absolute ethanol each and the filtrate is evaporated under reduced pressure. The residue is boiled with 50 ml of absolute isopropanol for 5 minutes and then filtered. The pH value of the filtrate is adjusted to 4 by adding 25% ethanolic hydrogen chloride solution under stirring and cooling with ice. The mixture is kept at 4° C. overnight, the crystalline precipitate is filtered off, washed with ice-cool absolute ethanol and dried to give 17 g (63% yield) of the aimed product, m. p. 131°-132° C. After recrystallization from ethanol, the hydrochloride melts at 133°-136° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. washwashed 3 times with 20 ml of absolute ethanol each and the filtrate
  3. customis evaporated under reduced pressure
  4. filtrationfiltered
  5. additionby adding 25% ethanolic hydrogen chloride solution
  6. temperaturecooling with ice
  7. waitThe mixture is kept at 4° C. overnight
  8. filtrationthe crystalline precipitate is filtered off
  9. washwashed with ice-
  10. temperaturecool absolute ethanol
  11. customdried

Sources & evidence

ORD record
ord-0289d308be124915b3dbd76124f1e903
Source dataset
uspto-grants-1989_05
Patent number
US04826845

Reaction notes

Loading…