4-(4-bromophenyl)phthalazin-1(2h)-one → HCID 67161042, compound

HRID 469516Notes

Reaction equation

HRID 469516 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[NH:10][N:9]=2)=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].C1(P(O[NH2:40])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1.CN(C=O)C.CCOC(C)=O>[NH2:40][N:10]1[N:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:18]

Participants

7

Reactant 3

HCID 6890724-(4-bromophenyl)phthalazin-1(2h)-oneHCID 10955453O-(Diphenylphosphinyl)hydroxylamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 67161042HCID 67161042, compoundYield 144.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(4-bromophenyl)phthalazin-1(2H)-one (Aldrich) (0.200 g, 0.663 mmol) and KOtBu (1 M in THF, 1.0 mL, 1.0 mmol) in THF (2 mL) was stirred for 45 minutes, diluted with DMF (1 mL), and O-(diphenylphosphoryl)hydroxylamine (0.240 g, 1.03 mmol) was added and stirred for 90 minutes. The mixture was diluted with EtOAc, washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4), and concentrated to give 302 mg of crude material as a white solid, which was used without purification. LC/MS (APCI) M/Z 318.0 (M+H)+.

Workup

  1. additionwas added
  2. stirringstirred for 90 minutes
  3. washwashed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e584af344a204411996967df614336b6
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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