HCID 86734410, compound → HCID 86734408, compound

HRID 1415103Notes

Reaction equation

HRID 1415103 reaction equation
[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH2:6]([O:8][C:9]([C:11]1[CH:12]([CH3:25])[CH2:13][CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[NH+:17]([CH3:24])[C:16]=12)=[O:10])[CH3:7]>CC(N(C)C)=O.[Pd]>[Cl:1]([O-:5])(=[O:4])(=[O:3])=[O:2].[CH2:6]([O:8][C:9]([C:11]1[C:12]([CH3:25])=[CH:13][CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[NH+:17]([CH3:24])[C:16]=12)=[O:10])[CH3:7]

Participants

4

Reactant 1

HCID 86734410HCID 86734410, compound

Product 1

HCID 86734408HCID 86734408, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 31374DimethylacetamideSolvent

Procedure

4-Ethoxycarbonyl-1,2-dihydro-3,5-dimethyl-5H-pyrido[1,2-a]benzimidazolium perchlorate (2.22g; 0.006 mole) is refluxed for an hour with stirring in (DMA) dimethylacetamide (40ml) containing (Pd/C) palladium on carbon (10%) (about .4g). The mixture is cooled, filtered, and poured into stirred ether. After an hour the solid is filtered, washed with ether, and dried to give 1.58g (71.5%). Recrystallized from ethanol to give 1.18g (53.5%); m.p. 242°-245° d.

Workup

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. additionpoured
  4. filtrationAfter an hour the solid is filtered
  5. washwashed with ether
  6. customdried
  7. customto give 1.58g (71.5%)
  8. customRecrystallized from ethanol
  9. customto give 1.18g (53.5%)

Sources & evidence

ORD record
ord-9e95e6fa2c78432e8799819ed71be478
Source dataset
uspto-grants-1977_01
Patent number
US04003750

Reaction notes

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