Acetic Acid → 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one

HRID 2069854Notes

Reaction equation

HRID 2069854 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([F:14])[CH:13]=1)[C:10](=O)[O:9][CH:8]2O)([CH3:4])([CH3:3])[CH3:2].O.[NH2:18][NH2:19].C(O)(=O)C>O>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([F:14])[CH:13]=1)[C:10](=[O:9])[NH:19][N:18]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 59473796HCID 59473796, compound

Product 1

HCID 594737656-(tert-Butyl)-8-fluorophthalazin-1(2H)-oneYield 75.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.2 g (5.4 mmol) of 5-tert-butyl-7-fluoro-3-hydroxy-3H-isobenzofuran-1-one was weighed into a 25 mL round bottom flask fitted with a stir bar, condenser, and nitrogen inlet. Added 7.5 mL (100 mmol) of hydrazine monohydrate. Added 10 mL of glacial acetic acid. Stirred under nitrogen at 100° overnight. Poured the reaction mixture into 100 ml, of stirred water. Extracted the aqueous mixture with 2×50 mL CH2Cl2. Dried the combined extracts over Na2SO4 and removed the solvent on the rotavap. Purified by silica gel flash chromatography using gradient elution with 0→100% EtOAc/CH2Cl2 to obtain 898 mg of the title compound as an off-white solid. MS (ESI) 221 (M+H)+.

Workup

  1. customfitted with a stir bar, condenser, and nitrogen inlet
  2. additionPoured the reaction mixture into 100 ml
  3. extractionExtracted the aqueous mixture with 2×50 mL CH2Cl2
  4. dry with materialDried the combined extracts over Na2SO4
  5. customremoved the solvent on the rotavap
  6. customPurified by silica gel flash chromatography
  7. washelution with 0→100% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-996f1c3460684e27a3c85b1031f658d3
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

Loading…