HCID 178526401, compound → 1H-Indolamine

HRID 2097668Notes

Reaction equation

HRID 2097668 reaction equation
O=CC([NH-])=O.[N+:6]([C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)([O-])=O>[NH4+].[Cl-].CCO.[Fe]>[NH2:6][C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

4

Reactant 1

HCID 178526401HCID 178526401, compound

Product 1

HCID 1220741H-Indolamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21115337HCID 21115337, compoundSolvent

Procedure

Reduction of nitro group to amine group used one of the following methods. Method A: Nitro indole 2-oxoacetyl amide and catalytic amount of palladium on carbon (Pd—C) was mixed in EtOH. The mixture was hydrogenated using Parr reactor under hydrogen pressure of 40-50 psi at room temperature for 24 hours. Then, solid was removed via filtration and filtrate was concentrated under vacuum to give crude amino indole 2-oxoacetyl amide which could be used as was or purified by silica gel chromatography. Method B: An excess of Fe (10-50 eq.) was added into the solution of nitro indole 2-oxoacetyl amide in saturated aqueous NH4Cl-EtOH (volume 1:1). The mixture was stirred at room temperature to 115° C. for 24 hours to 3 days. Solid was removed via filtration and solvents were removed under vacuum. Then, the residue was partitioned between water and EtOAc (equal volume to solvents used in reaction). The aqueous phase was extracted with EtOAc (3×e equal volume to solvents used in reaction). The combined organic phase was dried over MgSO4, filtered and concentrated under vacuum to give a crude amino indole 2-oxoacetyl amide which could be used as was or purified by silica gel chromatography.

Workup

  1. custompurified by silica gel chromatography
  2. customSolid was removed via filtration and solvents
  3. customwere removed under vacuum
  4. customThen, the residue was partitioned between water and EtOAc (equal volume to solvents used in reaction)
  5. extractionThe aqueous phase was extracted with EtOAc (3×e equal volume to solvents used in reaction)
  6. dry with materialThe combined organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-bd0e0c572b2a4eab8d685527b6bb7a37
Source dataset
uspto-grants-2013_05
Patent number
US08450361B2

Reaction notes

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