HCID 54510564, compound → HCID 15435225, compound

HRID 582843Notes

Reaction equation

HRID 582843 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([C:13]2[C:21]3[C:20](=[O:22])[CH2:19][CH2:18][CH2:17][C:16]=3[NH:15][C:14]=2[N+:23]([O-])=O)=[O:12])=[CH:6][CH:5]=1)[CH3:2]>[Pd].C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([C:13]2[C:21]3[C:20](=[O:22])[CH2:19][CH2:18][CH2:17][C:16]=3[NH:15][C:14]=2[NH2:23])=[O:12])=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 1

HCID 54510564HCID 54510564, compound

Product 1

HCID 15435225HCID 15435225, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-(4-Ethoxyphenyl)-2-nitro-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide (41 mg) was treated with 10% palladium on carbon (5 mg) in ethyl alcohol (10 mL) under hydrogen (50 PSI) in a Parr bottle for 1 hour. The mixture was filtered through Celite, concentrated in vacuo, and purified on Silica gel (5% methyl alcohol/dichloromethane) to afford N-(4-ethoxyphenyl)-2-amino-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide (Compound 57) (12 mg).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. custompurified on Silica gel (5% methyl alcohol/dichloromethane)

Sources & evidence

ORD record
ord-64cc302941154b4bad25c92d20ab67ec
Source dataset
uspto-grants-1999_07
Patent number
US05925770

Reaction notes

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