Ammonium formate → HCID 22144642, compound

HRID 1824997Notes

Reaction equation

HRID 1824997 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:7]2)([O-])=O.C([O-])=O.[NH4+]>C(OCC)(=O)C.C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:7]2

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 22144629HCID 22144629, compound

Product 1

HCID 22144642HCID 22144642, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

300 mg (0.97 mmol) of ethyl 5-nitro-1-phenyl-1H-indole-2-carboxylate from Example LVI are initially charged in 40 ml of ethyl acetate and 40 ml of ethanol. 365 mg (5.80 mmol) of ammonium formate and 102 mg of palladium on activated carbon (10%) are added. The mixture is heated to reflux, and at 50° C. gas evolves. After 4 hours at reflux, the mixture is cooled and filtered off through kieselguhr, which is washed with 500 ml of ethanol. The solvent is removed under reduced pressure and the residue is dried.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux
  3. customat 50° C.
  4. temperatureAfter 4 hours at reflux
  5. temperaturethe mixture is cooled
  6. filtrationfiltered off through kieselguhr, which
  7. washis washed with 500 ml of ethanol
  8. customThe solvent is removed under reduced pressure
  9. customthe residue is dried

Sources & evidence

ORD record
ord-615a23e3b263472ea9f70ac4c66c2dde
Source dataset
uspto-grants-2006_05
Patent number
US07045544B2

Reaction notes

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