Acetic Acid → 2-(4-tert-butyl-phenyl)-8-nitro-2H-phthalazin-1-one

HRID 133104Notes

Reaction equation

HRID 133104 reaction equation
CO[C:3](=[O:15])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:13]=O.Cl.[C:17]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][NH2:28])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].CC(O)=O.O1CCOCC1>CCOC(C)=O.CCCCCC>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([N:27]2[N:28]=[CH:13][C:5]3[C:4](=[C:9]([N+:10]([O-:12])=[O:11])[CH:8]=[CH:7][CH:6]=3)[C:3]2=[O:15])=[CH:25][CH:26]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 312751,4-DioxaneHCID 346007Methyl 2-formyl-6-nitrobenzoateHCID 162174584-Tert-butylphenylhydrazine hydrochloride

Product 1

HCID 691588672-(4-tert-butyl-phenyl)-8-nitro-2H-phthalazin-1-one

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

A solution of the aldehyde (Step C, 0.58 g, 3.3 mmol), 4-t-butylphenylhydrazine-HCl (0.66 g, 3.3 mmol), AcOH (1 mL), and dioxane (3 mL) in a sealed reaction vial was heated at 200° C. for 20 min in a microwave. Upon cooling, the residue was diluted with EtOAc (10 mL), then hexane (10 mL). The resulting precipitate was filtered to afford the desired compound as a tan solid. MS m/e 324 (M+H)+. Calc'd for C18H17N3O3-323.35.

Workup

  1. temperatureUpon cooling
  2. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-54fbdaa401e24893ab3ede98b6b1979f
Source dataset
uspto-grants-2008_06
Patent number
US07390820B2

Reaction notes

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