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Dimethylformamide → 2-amino-4-phenylphthalazin-1(2H)-one

HRID 469534
Notes
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Reaction equation

HRID 469534 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC([O-])(C)C.[K+].C[N:25](C=O)C.C1(P(ON)(C2C=CC=CC=2)=O)C=CC=CC=1>CCOC(C)=O>[NH2:25][N:9]1[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 2191504-Phenyl-1-(2H)-phthalazinoneHCID 10955453O-(Diphenylphosphinyl)hydroxylamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 212625372-amino-4-phenylphthalazin-1(2H)-oneYield 95%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

A mixture of 4-phenylphthalazin-1(2H)-one (Aldrich) (500 mg, 2.25 mmol) and KOtBu (3.37 mL, 3.37 mmol) was stirred for 45 minutes, diluted with DMF for solubility, and Example 17A (787 mg, 3.37 mmol) was added and stirred for 3 hours. The mixture was diluted with EtOAc, washed with saturated NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated to give 509 mg (95%) of the title compound. MS (DCI/NH3) m/z 238 (M+H)+.

Workup

  1. additionwas added
  2. stirringstirred for 3 hours
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8c387b1a38c74ff5b40ca8df2d698c73
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08629143B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes