Dimethyl Sulfoxide → 2-amino-5-[pyridazin-3(2H)-on-6-yl]indane hydrobromide

HRID 1451770Notes

Reaction equation

HRID 1451770 reaction equation
[BrH:1].C(O)(=O)C.[NH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:16]3[CH2:17][CH2:18][C:19](=[O:22])[NH:20][N:21]=3)[CH:13]=2)[CH2:8]1.CS(C)=O>C(OCC)C>[BrH:1].[NH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:16]3[CH:17]=[CH:18][C:19](=[O:22])[NH:20][N:21]=3)[CH:13]=2)[CH2:8]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 140714996-(2-amino-indan-5-yl)-4,5-dihydropyridazin-3(2H)-oneHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 189297722-amino-5-[pyridazin-3(2H)-on-6-yl]indane hydrobromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In 70 ml of a 25% hydrogen bromide-acetic acid solution was suspended 8.02 g of 2-amino-5-[4,5-dihydropyridazin-3(2H)-on-6-yl]indane, and 2.96 g of dimethyl sulfoxide was added to the suspension under ice cooling. The mixture was stirred at room temperature for 1.5 hours. Then, 140 ml of diethyl ether was added to the reaction mixture, and crystals precipitated were collected by filtration and recrystallized from methanol to obtain 8.55 g of 2-amino-5-[pyridazin-3(2H)-on-6-yl]indane hydrobromide.

Workup

  1. additionwas added to the suspension under ice cooling
  2. customprecipitated
  3. filtrationwere collected by filtration
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-b142cfa7e89f42c195d129056ddb6136
Source dataset
uspto-grants-1997_02
Patent number
US05605901

Reaction notes

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