Ammonium formate → HCID 10039871, compound

HRID 847506Notes

Reaction equation

HRID 847506 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[C:11](=[O:22])[C:12](=[CH:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH2:13][CH2:14][C:3]=12.C([O-])=O.[NH4+]>[Pd].C(O)(=O)C>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[C:11](=[O:22])[CH:12]([CH2:15][C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH2:13][CH2:14][C:3]=12

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 54337016HCID 54337016, compound

Product 1

HCID 10039871HCID 10039871, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 8,9-dihydro-10-methyl-7-[(pyridin-3-yl)-methylene]pyrido[1,2-a]indol-6(7H)-one (520 mg), ammonium formate (568 mg) and 10% palladium on carbon (200 mg) in acetic acid (20 ml) was stirred at 110° C. for 2 hours. After filtration of the catalyst, the filtrate was evaporated in vacuo. The residue was diluted with 10% methanol-chloroform. The solution was washed with 5% aqueous solution of sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. Purification of the residue with silica gel chromatography (5% methanol-chloroform), followed by recrystallization from ethyl acetate-ether, gave 8,9-dihydro-10-methyl-7-[(pyridin-3-yl)methyl]pyrido[1,2-a]indol-6(7H)-one (273 mg).

Workup

  1. filtrationAfter filtration of the catalyst
  2. customthe filtrate was evaporated in vacuo
  3. additionThe residue was diluted with 10% methanol-chloroform
  4. washThe solution was washed with 5% aqueous solution of sodium hydrogencarbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customPurification of the residue with silica gel chromatography (5% methanol-chloroform)
  8. customfollowed by recrystallization from ethyl acetate-ether

Sources & evidence

ORD record
ord-3fd3f43416d747b8b5d11bef9232220c
Source dataset
uspto-grants-1992_08
Patent number
US05141945

Reaction notes

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