Sodium Hydroxide → HCID 178524810, compound

HRID 1408915Notes

Reaction equation

HRID 1408915 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9]([OH:10])=[C:8]([C:11]([O:13]CC)=[O:12])[CH:7]=[N:6][N:5]2[CH:16]=1.[OH-].[Na+]>CO.C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9]([OH:10])=[C:8]([C:11]([OH:13])=[O:12])[CH:7]=[N:6][N:5]2[CH:16]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178469953HCID 178469953, compound

Product 1

HCID 178524810HCID 178524810, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl 6-fluoro-4-hydroxypyrrolo[1,2-b]pyridazine-3-carboxylate (700 mg, 3.12 mmol) in methanol (3 mL) and THF (3 mL) was added 3 N aq. sodium hydroxide (5.20 mL, 15.61 mmol) and the resulting mixture was stirred at 65° C. for 3 h. The mixture was cooled and concentrated to remove the methanol and THF and the obtained residue was cooled in an ice bath and 3N aq. HCl was added dropwise with stirring until pH of the mixture was ˜2. The resulting slurry was stirred for 30 min, and filtered to collect the solid. The solid was rinsed with water and dried to afford 550 mg (90%) of the title compound as a white solid. HPLC (condition B): retention time=2.37 min. LCMS (condition B): m/z 197+ve.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customto remove the methanol and THF
  4. temperaturethe obtained residue was cooled in an ice bath
  5. addition3N aq. HCl was added dropwise
  6. stirringwith stirring until pH of the mixture
  7. stirringThe resulting slurry was stirred for 30 min
  8. filtrationfiltered
  9. customto collect the solid
  10. washThe solid was rinsed with water
  11. customdried

Sources & evidence

ORD record
ord-d6788957dad044798c711a02c4226b79
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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