Hydrazine hydrate (1:1) → 6-fluoro-4-phenylphthalazin-1(2H)-one

HRID 469551Notes

Reaction equation

HRID 469551 reaction equation
O.[NH2:2][NH2:3].[C:4]([C:12]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:13]=1[C:14](OC)=[O:15])(=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CCO>[F:22][C:20]1[CH:21]=[C:12]2[C:13](=[CH:18][CH:19]=1)[C:14](=[O:15])[NH:3][N:2]=[C:4]2[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67161783Methyl 2-benzoyl-4-fluorobenzoate

Product 1

HCID 671600626-fluoro-4-phenylphthalazin-1(2H)-oneYield 81.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of hydrazine hydrate (0.26 mL, 4.6 mmol) and the product of example 35C (0.390 g, 1.5 mmol) in EtOH (4.5 mL) was stirred at 80° C. for 3 hours, concentrated, and chromatographed on SiO2 (3% MeOH/CH2Cl2) to give 293.5 mg of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 12.93 (s, 1H), 8.42 (dd, 1H), 7.76 (ddd, 1H), 7.53-7.63 (m, 5H), 7.32 (dd, 1H).

Workup

  1. concentrationconcentrated
  2. customchromatographed on SiO2 (3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-216021a03c924278aa7f985186f9ef0f
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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