Hydrochloric Acid → 6-(tetrahydroquinoline-1-sulfonyl)-2H-pyridazin-3-one

HRID 22757Notes

Reaction equation

HRID 22757 reaction equation
C[O:2][C:3]1[N:4]=[N:5][C:6]([S:9]([N:12]2[C:21]3[CH:16]([CH2:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:7][CH:8]=1.Cl>O1CCOCC1>[N:12]1([S:9]([C:6]2[CH:7]=[CH:8][C:3](=[O:2])[NH:4][N:5]=2)(=[O:11])=[O:10])[C:21]2[CH:16]([CH2:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 690499883-Methoxy-6-(tetrahydroquinoline-1-sulfonyl)-pyridazine

Product 1

HCID 690507546-(tetrahydroquinoline-1-sulfonyl)-2H-pyridazin-3-oneYield 33%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-methoxy-6-(tetrahydroquinoline-1-sulfonyl)-pyridazine (1.14 mmol, 112 mg), conc. HCl (2 mL), and dioxane (5 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 extracted with EtOAc. The EtOAc extract was washed with water, collected, dried, filtered and the filtrate was evaporated to a residue, which was crystallized from ether to yield 6-(tetrahydroquinoline-1-sulfonyl)-2H-pyridazin-3-one (33%, 11 mg); mp 200° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated to dryness
  3. additionWater (10 mL) was added to the residue
  4. extractionextracted with EtOAc
  5. extractionThe EtOAc extract
  6. washwas washed with water
  7. customcollected
  8. customdried
  9. filtrationfiltered
  10. customthe filtrate was evaporated to a residue, which
  11. customwas crystallized from ether

Sources & evidence

ORD record
ord-0bb9b2df07964b0fb8f7e33ed104510b
Source dataset
uspto-grants-2005_02
Patent number
US06849629B2

Reaction notes

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