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Ammonium formate → 5-Amino-N-phenyl-1-(2-phenylethyl)-1H-indole-2-carboxamide

HRID 1824992
Notes
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Reaction equation

HRID 1824992 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]([C:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22])=[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]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:8]([C:21]([NH:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:22])=[CH:7]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 221446385-Nitro-N-phenyl-1-(2-phenylethyl)-1H-indole-2-carboxamide

Product 1

HCID 221446705-Amino-N-phenyl-1-(2-phenylethyl)-1H-indole-2-carboxamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

50 mg (0.13 mmol) of 5-nitro-N-phenyl-1-(2-phenylethyl)-1H-indole-2-carboxamide from Example XLIX are initially charged in 7 ml of ethyl acetate and 7 ml of ethanol. 49 mg (0.78 mmol) of ammonium formate and 14 mg of palladium on activated carbon 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 through kieselguhr, which is then washed with 500 ml of ethanol. The solvent is removed under reduced pressure and the residue is dried. This gives 115 mg of a white solid which still contains inorganic salts and which is reacted further without purification.

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 through kieselguhr, which
  7. washis then washed with 500 ml of ethanol
  8. customThe solvent is removed under reduced pressure
  9. customthe residue is dried
  10. customThis gives 115 mg of a white solid which still contains inorganic salts and which is reacted further without purification

Sources & evidence

ORD record
ord-59676dbada384896a2ac1cbd86827a24
Source dataset
uspto-grants-2006_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07045544B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes