2-Benzyloxy-5-methyl-benzo[de]isoquinoline-1,3-dione → 2-Hydroxy-5-methyl-benzo[de]isoquinoline-1,3-dione

HRID 279000Notes

Reaction equation

HRID 279000 reaction equation
C([O:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([CH3:23])[CH:22]=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:24])C1C=CC=CC=1>CC(N(C)C)=O.[Pd]>[OH:8][N:9]1[C:18](=[O:19])[C:17]2[CH:20]=[C:21]([CH3:23])[CH:22]=[C:15]3[C:16]=2[C:11](=[CH:12][CH:13]=[CH:14]3)[C:10]1=[O:24]

Participants

4

Reactant 1

HCID 226240502-Benzyloxy-5-methyl-benzo[de]isoquinoline-1,3-dione

Product 1

HCID 226239402-Hydroxy-5-methyl-benzo[de]isoquinoline-1,3-dioneYield 33.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 31374DimethylacetamideSolvent

Procedure

The hydrogenation of 2-benzyloxy-5-methyl-benzo[de]isoquinoline-1,3-dione (0.4 g, 1.3 mmol, from Example P) was performed in the presence of 10% Pd/C (0.1 g) in DMA (20 mL). Purification of crude product by column chromatography (silica gel using 10% methanol in dichloromethane) gave 0.1 g of the title compound, mp 251-253° C.;

Workup

  1. customPurification of crude product by column chromatography (silica gel using 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-33a6d9159eb1442482fa8c04391dedde
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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