Triethylamine → 2-Tert-butyldimethylsilyoxy-5-nitro-benzo[de]isoquinoline-1,3-dione

HRID 278950Notes

Reaction equation

HRID 278950 reaction equation
C(N(CC)CC)C.[Si:8](Cl)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[OH:16][N:17]1[C:26](=[O:27])[C:25]2[CH:28]=[C:29]([N+:31]([O-:33])=[O:32])[CH:30]=[C:23]3[C:24]=2[C:19](=[CH:20][CH:21]=[CH:22]3)[C:18]1=[O:34]>C(Cl)(Cl)Cl>[Si:8]([O:16][N:17]1[C:26](=[O:27])[C:25]2[CH:28]=[C:29]([N+:31]([O-:33])=[O:32])[CH:30]=[C:23]3[C:24]=2[C:19](=[CH:20][CH:21]=[CH:22]3)[C:18]1=[O:34])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 2721422-Hydroxy-5-(hydroxy(oxido)amino)-1H-benzo(de)isoquinoline-1,3(2H)-dione

Product 1

HCID 1317222782-Tert-butyldimethylsilyoxy-5-nitro-benzo[de]isoquinoline-1,3-dioneYield 75.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Triethyl amine (0.4 g, 4.0 mmol) and tert-butyldimethylsilyl chloride (0.6 g, 4.0 mmol) were added to a solution of 2-hydroxy-5-nitro-benzo[de]isoquinoline-1,3-dione (1.0 g, 3.9 mmol, from Example 1) in chloroform (10 mL). The mixture was stirred at room temperature for 3 hours and concentrated in vacuo to give a dark residue. Column chromatography (silica gel 2% methanol in chloroform) gave 1.1 g of the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a dark residue

Sources & evidence

ORD record
ord-5654f0b67e7d4e7caba417dbe159c131
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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