Benzyl Bromide → HCID 21106525, compound

HRID 1765341Notes

Reaction equation

HRID 1765341 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[NH:4][N:3]=1.[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH2:15]([N:4]1[N:3]=[C:2]([Br:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:12])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 6143104-bromo-2H-phthalazin-1-one

Product 1

HCID 21106525HCID 21106525, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

4-Bromo-2H-phthalazin-1-one (10.38 g, 46 mmol) was dissolved in dimethylformamide (DMF) (60 ml). To this was added NaH (60%, 1.55 g, 46.2 mmol) as a DMF suspension (20 ml). The mixture was stirred at room temperature for 30 mins then benzyl bromide (13.82 g, 50.8 mmol) was added in one portion as a solution in DMF (20 ml). The reaction mixture was stirred for 2 hours then the DMF was removed under reduced pressure and the resulting crude material purified by column chromatography (gradient elution: 100% heptane to 20% ethyl acetate: heptane) to give the title compound (8.16 g, 56% yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO), 8.30 (1H, dd), 8.03 (1H, ddd), 7.97–7.91 (2H, m), 7.34–7.27 (5H, m), 5.31 (2H, s); MS (ESI+)=(M+H)+ 315 & 317

Workup

  1. stirringThe reaction mixture was stirred for 2 hours
  2. customthe DMF was removed under reduced pressure
  3. customthe resulting crude material purified by column chromatography (gradient elution: 100% heptane to 20% ethyl acetate: heptane)

Sources & evidence

ORD record
ord-70271417c1c046d9839dfc038e189424
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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