Hydrochloric Acid → Levosimendan

HRID 1467372

Reaction equation

HRID 1467372 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.Cl.[N:17]([O-])=O.[Na+].[C:21](#[N:25])[CH2:22][C:23]#[N:24].C([O-])(=O)C.[Na+]>>[CH3:15][C@H:9]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][N:17]=[C:22]([C:21]#[N:25])[C:23]#[N:24])=[CH:3][CH:4]=2)=[N:13][NH:12][C:11](=[O:14])[CH2:10]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 161928Ici 109,081HCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 3033825LevosimendanYield 82.3%

Procedure

To a solution of (−)-6-(4-aminophenyl)-4,5-dihydro-5-methyl-3-(2H)-pyridazinone (20 g) and dilute hydrochloric acid (52 ml of concentrated hydrochloric acid in 789 ml of water), 8 g of dilute sodium nitrite (8 g of sodium nitrite in 52 ml of water) was added and stirred. After 10 minutes, malononitrile solution (6.3 g malononitrile in 52 ml of water) was added. The solution was stirred for 1 hour at room temperature. The pH of the suspension was adjusted to 6.0 with sodium acetate solution. The suspension was filtered, washed with water followed by ethanol and then dried to obtain solid levosimendan (yield—22 g, purity—99.9%).

Workup

  1. stirringThe solution was stirred for 1 hour at room temperature
  2. filtrationThe suspension was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-4647ec44381243a985154d5e0c3f01f6
Source dataset
uspto-grants-2015_04
Patent number
US09000158B2

Linked notes

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