Acetic Acid → 6-(tert-butyl)phthalazin-1(2H)-one

HRID 68463Notes

Reaction equation

HRID 68463 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=O)[O:9][CH:8]2OCC)([CH3:4])([CH3:3])[CH3:2].O.[NH2:19][NH2:20].C(O)(=O)C>O>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:9])[NH:20][N:19]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 580162095-tert-Butyl-3-ethoxy-3H-isobenzofuran-1-one

Product 1

HCID 576339336-(tert-butyl)phthalazin-1(2H)-oneYield 92.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.9 g (12 mmol) of 5-tert-butyl-3-ethoxy-3H-isobenzofuran-1-one was weighed into a 50 mL round bottom flask fitted with a stir bar and cap. Added 10 mL (130 mmol) of hydrazine monohydrate. Added 15 mL of glacial acetic acid. Stirred at 100° overnight. Poured the reaction mixture into 200 mL of stirred water. Collected the solids by filtration and washed with water. Dried under high vacuum to obtain 2.24 g of the title compound as an off-white solid. MS (ESI) 203 (M+H)+.

Workup

  1. customfitted with a stir bar
  2. customcap
  3. customCollected the solids
  4. filtrationby filtration
  5. washwashed with water
  6. customDried under high vacuum

Sources & evidence

ORD record
ord-d34e3477313b4297b02b331df6282e73
Source dataset
uspto-grants-2014_09
Patent number
US08822457B2

Reaction notes

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