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

HRID 566963

Reaction equation

HRID 566963 reaction equation
[C:1]([Si:5]([CH3:9])([CH3:8])[O:6][NH2:7])([CH3:4])([CH3:3])[CH3:2].[CH:10]1[CH:19]=[C:18]2[C:20]([O:22][C:23](=O)[C:16]3=[C:17]2[C:12](=[CH:13][C:14]([N+:25]([O-:27])=[O:26])=[CH:15]3)[CH:11]=1)=[O:21]>N1C=CC=CC=1>[Si:5]([O:6][N:7]1[C:23](=[O:22])[C:16]2[CH:15]=[C:14]([N+:25]([O-:27])=[O:26])[CH:13]=[C:12]3[C:17]=2[C:18](=[CH:19][CH:10]=[CH:11]3)[C:20]1=[O:21])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 18194Naphthalic anhydride, 3-nitro-HCID 4691350O-(tert-Butyldimethylsilyl)hydroxylamine

Product 1

HCID 1317222782-Tert-butyldimethylsilyoxy-5-nitro-benzo[de]isoquinoline-1,3-dioneYield 85.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

O-(tert-Butyldimethyl-silyl)hydroxylamine (1.8 g, 12.3 mmol) was added to a solution of 3-nitro-1,8-naphthalic anhydride (2.0 g, 8.2 mmol) in 50 mL of pyridine. The solution was refluxed for 4 hours and concentrated in vacuo. Purification as described in Example A-1 gave 2.6 g of the title compound.

Workup

  1. temperatureThe solution was refluxed for 4 hours
  2. concentrationconcentrated in vacuo
  3. customPurification

Sources & evidence

ORD record
ord-08316885c60c4f95938146a1dd7a2269
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Linked notes

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