5,10-Dihydro-pyrido[3,4-g]isoquinoline → Pyrido(3,4-g)isoquinoline

HRID 1534974Notes

Reaction equation

HRID 1534974 reaction equation
[CH:1]1[C:6]2[CH2:7][C:8]3[CH:9]=[CH:10][N:11]=[CH:12][C:13]=3[CH2:14][C:5]=2[CH:4]=[CH:3][N:2]=1>COC(OC)COCC(OC)OC.[Pd]>[CH:12]1[C:13]2=[CH:14][C:5]3[CH:4]=[CH:3][N:2]=[CH:1][C:6]=3[CH:7]=[C:8]2[CH:9]=[CH:10][N:11]=1

Participants

4

Reactant 1

HCID 150416215,10-Dihydro-pyrido[3,4-g]isoquinoline

Product 1

HCID 13064692Pyrido(3,4-g)isoquinoline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 554377Ethane, 1,1'-oxybis[2,2-dimethoxy-Solvent

Procedure

1.6 g of 5,10-dihydro-pyrido[3,4-g]isoquinoline and 0.32 g of palladium-on-charcoal was dispersed and mixed in 100 cc of dimethoxyethyl ether, and refluxed for 15 hours under argon atmosphere. After the filtration of palladium-on-charcoal and solvent was evaporated to obtain crude pyrido[3,4-g]isoquinoline. The product was purified by preparative liquid chromatography (gel; R-055-15, S16SIL, YMC Ltd., developing solvent; ethyl alcohol/benzene=3/7). The yield of the compound was 1.3 g (95%) and its m.p. was 174° C. The compound was identified as pyrido [3,4-g]isoquinoline based upon the following elemental analysis.

Workup

  1. temperaturerefluxed for 15 hours under argon atmosphere
  2. filtrationAfter the filtration of palladium-on-charcoal and solvent
  3. customwas evaporated

Sources & evidence

ORD record
ord-8f9d28b9e1c94cfb94b41bd23ca904a2
Source dataset
uspto-grants-1992_02
Patent number
US05091535

Reaction notes

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