HCID 18691150, compound → HCID 15462585, compound

HRID 376329Notes

Reaction equation

HRID 376329 reaction equation
[NH2:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]3[C:14]([C:5]2=[N:4][C:3]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])=[CH:13][C:12]([O:15]CC1C=CC=CC=1)=[CH:11][CH:10]=3.[H][H]>C(O)C.[Pd]>[NH2:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]3[C:14]([C:5]2=[N:4][C:3]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29])=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=3

Participants

5

Reactant 2

HCID 18691150HCID 18691150, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 15462585HCID 15462585, compoundYield 83.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5 g of 3-amino-9-benzyloxy-2-(2-methylphenyl)imidazo[2,1-a]isoquinoline (Compound 40) in 100 ml of ethanol was added 0.5 g of palladium on activated carbon (Pd 10%). After introduction of hydrogen, the mixture was stirred at room temperature for 24 hours. The reaction mixture was filtered, and the filtrate was evaporated in vacuo. Resultant residue was purified by column chromatography on silica gel and recrystallized from water/methanol to give 3.2 g of the title compound as pale yellow needles.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customResultant residue was purified by column chromatography on silica gel
  4. customrecrystallized from water/methanol

Sources & evidence

ORD record
ord-68e70ae6f5da4f70b02aeafbc1116ca6
Source dataset
uspto-grants-2000_02
Patent number
US06020342

Reaction notes

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