Hydrochloric Acid → 6-(1H-indole-2-sulfonyl)-2,3-dihydropyridazin-3-one

HRID 1369479Notes

Reaction equation

HRID 1369479 reaction equation
CO[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9]([C:12]2[NH:13][C:14]3[C:19]([CH:20]=2)=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:11])=[O:10])[NH:4]1.Cl.[O:22]1CCOCC1>>[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[C:12]1[S:9]([C:5]1[CH:6]=[CH:7][C:8](=[O:22])[NH:3][N:4]=1)(=[O:11])=[O:10]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 22591541HCID 22591541, compound

Product 1

HCID 98568096-(1H-indole-2-sulfonyl)-2,3-dihydropyridazin-3-oneYield 37%

Conditions

Temperature
100 °C

Procedure

A mixture of 2-methoxy-6-(indole-2-sulfonyl)-pyridazine (1.03 mmol, 300 mg), conc. HCl (1 mL), and dioxane (6 mL) was heated at 100° C. for two hours. The reaction mixture was cooled and evaporated to dryness. Water (10 mL) was added to the residue and the resulting solid was triturated with methanol (2 mL) to yield 6-(indole-2-sulfonyl)-2H-pyridazin-3-one (37%, 106 mg); mp 248° C.-249° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated to dryness
  3. additionWater (10 mL) was added to the residue
  4. customthe resulting solid was triturated with methanol (2 mL)

Sources & evidence

ORD record
ord-e62d0d45b13844f8aa9ffac9814203f3
Source dataset
uspto-grants-2003_06
Patent number
US06579879B2

Reaction notes

Loading…