Hydrazine hydrate (1:1) → 6-(tert-Butyl)-8-fluorophthalazin-1(2H)-one

HRID 2069713Notes

Reaction equation

HRID 2069713 reaction equation
[C:1]([C:5]1[CH:13]=[C:12]([F:14])[C:8]([C:9](O)=[O:10])=[C:7]([CH:15](OC)OC)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.[NH2:21][NH2:22]>C(O)C.C(O)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]2[C:8](=[C:12]([F:14])[CH:13]=1)[C:9](=[O:10])[NH:22][N:21]=[CH:15]2)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59473800HCID 59473800, compound

Product 1

HCID 594737656-(tert-Butyl)-8-fluorophthalazin-1(2H)-oneYield 86%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

4-tert-Butyl-2-dimethoxymethyl-6-fluoro-benzoic acid (220.3 g, 0.815 moles) was dissolved in ethanol (2 vol, 440 mL) and acetic acid (0.5 vol, 110 mL). Hydrazine hydrate (1.5 eq, 61 mL) was added and the solution stirred at 80° C. for 6 hours. The mixture was cooled to rt overnight, then in an ice bath and then filtered and washed with cold ethanol. The fine white crystals were dried at 100° C. in a vacuum oven with N2 sweep, to provide 154.7 g (86%) of 6-tert-butyl-8-fluoro-2H-phthalazin-1-one.

Workup

  1. temperatureThe mixture was cooled to rt overnight
  2. filtrationin an ice bath and then filtered
  3. washwashed with cold ethanol
  4. dry with materialThe fine white crystals were dried at 100° C. in a vacuum oven with N2 sweep

Sources & evidence

ORD record
ord-91afe247c11c47768d2e1c0e8b1723f0
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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