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

HRID 278952Notes

Reaction equation

HRID 278952 reaction equation
[Si:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([N+:23]([O-])=O)[CH:22]=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C>[NH2:23][C:21]1[CH:22]=[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:16]2=[C:17]([CH:20]=1)[C:18](=[O:19])[N:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[C:10]3=[O:26]

Participants

4

Reactant 1

HCID 1317222782-Tert-butyldimethylsilyoxy-5-nitro-benzo[de]isoquinoline-1,3-dione

Product 1

HCID 1317222805-Amino-2-tert-butyldimethylsilyoxy-benzo[de]isoquinoline-1,3-dioneYield 86.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The hydrogenation of 2-tert-butyldimethylsilyoxy-5-nitro-benzo[de]isoquinoline-1,3-dione (1.0 g, 2.7 mmol, from Example A-1 or A-2) at 40 psi in the presence of 10% Pd/C catalyst (1.0 g) in ethyl acetate (20 mL) afforded 0.8 g of the title compound.

Sources & evidence

ORD record
ord-bf15403a3e3e4498bc22b7453ef3f626
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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