2-Benzyloxy-5-bromo-benzo[de]isoquinoline-1,3-dione → 2-Benzyloxy-5-methyl-benzo[de]isoquinoline-1,3-dione

HRID 566969Notes

Reaction equation

HRID 566969 reaction equation
[CH3:1][Zn]C.[CH2:4]([O:11][N:12]1[C:21](=[O:22])[C:20]2[CH:23]=[C:24](Br)[CH:25]=[C:18]3[C:19]=2[C:14](=[CH:15][CH:16]=[CH:17]3)[C:13]1=[O:27])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:4]([O:11][N:12]1[C:21](=[O:22])[C:20]2[CH:23]=[C:24]([CH3:1])[CH:25]=[C:18]3[C:19]=2[C:14](=[CH:15][CH:16]=[CH:17]3)[C:13]1=[O:27])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 226238992-Benzyloxy-5-bromo-benzo[de]isoquinoline-1,3-dioneHCID 178477796HCID 178477796, compound

Product 1

HCID 226240502-Benzyloxy-5-methyl-benzo[de]isoquinoline-1,3-dione

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Dimethylzinc (4 mL, 2 eq.) was added to a suspension of 2-benzyloxy-5-bromo-benzo[de]isoquinoline-1,3-dione (1.5 g, 3.9 mmol, from Example O) and Pd(PPh3)2Cl2(0.14 g, 0.2 mmol) in dry THF (20 mL). The mixture was stirred under nitrogen at room temperature for 8 hours, filtered, and washed with dimethylacetamide. Concentration of the filtrate gave 1.1 g of the title compound in crude form which was used as is.

Workup

  1. filtrationfiltered
  2. washwashed with dimethylacetamide

Sources & evidence

ORD record
ord-00df9baeabc24930a4c0171477d636a7
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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