Acetyl chloride → N-[4-(4-Bromo-1-oxo-1H-phthalazin-2-yl)-phenyl]acetamide

HRID 1765379Notes

Reaction equation

HRID 1765379 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[N:21]=[C:20]([Br:22])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:23])=[CH:8][CH:7]=1>N1C=CC=CC=1>[Br:22][C:20]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[O:23])[N:12]([C:9]2[CH:10]=[CH:11][C:6]([NH:5][C:1](=[O:3])[CH3:2])=[CH:7][CH:8]=2)[N:21]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 211065172-(4-amino-phenyl)-4-bromo-2H-phthalazin-1-one

Product 1

HCID 21106602N-[4-(4-Bromo-1-oxo-1H-phthalazin-2-yl)-phenyl]acetamideYield 65%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetyl chloride (0.15 g, 1.90 mmol) was added at room temperature to a stirred solution of 2-(4-amino-phenyl)-4-bromo-2H-phthalazin-1-one (0.30 g, 0.95 mmol) in pyridine (3 ml). Stirring was continued for 12 h before the solvent was evaporated in vacuum. The resulting raw product was dissolved in H2O and the title compound was collected by filtration (0.22 g, 65% yield). 1H-NMR: (400 MHz, D6-DMSO) 10.16 (1H, s), 8.37 (1H, d), 8.08 (1H, t), 8.00–8.03 (2H, m), 7.72 (2H, d), 7.52 (2H, d), 2.05 (3H, s); MS (ESI+)=358.15 (M+H)+.

Workup

  1. customwas evaporated in vacuum
  2. dissolutionThe resulting raw product was dissolved in H2O
  3. filtrationthe title compound was collected by filtration (0.22 g, 65% yield)

Sources & evidence

ORD record
ord-79545f35427f4681b5a741c300b094bf
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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