2-Benzyloxy-5-cyano-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione → 5-Cyano-2-hydroxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione

HRID 279018Notes

Reaction equation

HRID 279018 reaction equation
C([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([C:29]#[N:30])[C:22]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:31])C1C=CC=CC=1.[H][H]>C1COCC1.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[C:29]([C:21]1[C:22]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[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]([OH:8])[C:10]3=[O:31])#[N:30]

Participants

5

Reactant 2

HCID 226239712-Benzyloxy-5-cyano-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dioneHCID 178418361HCID 178418361, compound

Product 1

HCID 226239785-Cyano-2-hydroxy-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dioneYield 45.9%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-benzyloxy-5-cyano-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.16 g, 0.40 mmol, from Example D2) and 5% Pd/BaSO4 (0.05 g) in THF (75 mL) was shaken in an atmosphere of hydrogen at 50 psi at ambient temperature for 86 hours with an additional 0.05 g of 5% Pd/BaSO4 being added after 70 hours. The catalyst was removed by filtration and the filtrate evaporated under reduced pressure. The residue was chromatographed on silica using chloroform/methanol (10:1) to give 0.059 g of the title compound, mp >250° C.

Workup

  1. additionadded after 70 hours
  2. customThe catalyst was removed by filtration
  3. customthe filtrate evaporated under reduced pressure
  4. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-04d0c76f074749d4a8b44bf59eb3c932
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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