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

HRID 567005Notes

Reaction equation

HRID 567005 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:5]2=[C:6]([CH:24]=1)[C:7](=[O:23])[N:8]([O:15][Si](C(C)(C)C)(C)C)[C:9]3=[O:14]>Cl.C(O)C>[NH2:1][C:2]1[CH:3]=[C:4]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:5]2=[C:6]([CH:24]=1)[C:7](=[O:23])[N:8]([OH:15])[C:9]3=[O:14]

Participants

4

Reactant 1

HCID 1317222805-Amino-2-tert-butyldimethylsilyoxy-benzo[de]isoquinoline-1,3-dione

Product 1

HCID 7084445-Amino-2-hydroxy-benzo[de]isoquinoline-1,3-dioneYield 76.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of compound 5-amino-2-tert-butyldimethylsilyoxy-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline (0.8 g, 2.3 mmol, from Example B) in 2% HCl in ethanol (50 mL) was stirred at room temperature for 1 hour. The solid which formed was filtered and dried, to give 0.4 g of the title compound, mp 288-294° C. (dec).

Workup

  1. customThe solid which formed
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-7775001bab954f768c7a0e0c8d287260
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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