Ethyl 8,9-dimethoxy-3-methyl-2-(3-nitrophenyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carboxylate → Ethyl 2-(3-aminophenyl)-8,9-dimethoxy-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carboxylate

HRID 585079Notes

Reaction equation

HRID 585079 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]1=[C:15]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=3)=[C:17]([CH3:18])[N:8]1[CH2:7][CH2:6]2>CO.[Pd]>[NH2:25][C:21]1[CH:20]=[C:19]([C:16]2[C:15]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:9]3[C:10]4[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([O:13][CH3:14])[CH:11]=4)[CH2:6][CH2:7][N:8]3[C:17]=2[CH3:18])[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 1

HCID 10181470Ethyl 8,9-dimethoxy-3-methyl-2-(3-nitrophenyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carboxylate

Product 1

HCID 10179495Ethyl 2-(3-aminophenyl)-8,9-dimethoxy-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4.5 g (10.31 mmol) of ethyl 8,9-dimethoxy-3-methyl-2-(3-nitrophenyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carboxylate (Example 2) were dissolved in 500 mL of warm methanol, 2.03 g of 10% strength palladium on charcoal were added, and the compound was hydrogenated at atmospheric pressure. The reaction mixture was filtered through a filter aid, the filtrate was evaporated under reduced pressure to a volume of approx. 150 mL, and the resulting precipitate was filtered off to give the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through a filter aid
  2. customthe filtrate was evaporated under reduced pressure to a volume of approx. 150 mL
  3. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-729e568f7f774b43a340c911b10caa9d
Source dataset
uspto-grants-2005_08
Patent number
US06930114B2

Reaction notes

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