HCID 19600420, compound → HCID 19600382, compound

HRID 609759Notes

Reaction equation

HRID 609759 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][CH2:15][N:16]1[C:20](=[O:21])[C:19]3=[CH:22][CH:23]=[CH:24][CH:25]=[C:18]3[C:17]1=[O:26])[CH:8]=[CH:7]2)([O-])=O>[C].[Pd].CN(C)C=O>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][CH2:15][N:16]1[C:17](=[O:26])[C:18]3=[CH:25][CH:24]=[CH:23][CH:22]=[C:19]3[C:20]1=[O:21])[CH:8]=[CH:7]2

Participants

4

Reactant 1

HCID 19600420HCID 19600420, compound

Product 1

HCID 19600382HCID 19600382, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To 4.4 g of 5-nitro-1-(3-phthalimidopropyl)-indole was added 200 ml of dimethylformamide, further was added 0.15 g of 10% palladium-carbon and hydrogenized at 65° C., under the pressure of 4 kg/cm2, for 7 hours. After the reaction was finished, the reaction mixture was filtrated, and the solvent was removed by distillation under reduced pressure. The thus obtained residue was treated to a silica column chromatography (eluent: 3% methanol/dichloromethane) to obtain 3.4 g of 5-amino-1-(3-phthalimidopropyl)indole in the form of brown needle crystals.

Workup

  1. filtrationthe reaction mixture was filtrated
  2. customthe solvent was removed by distillation under reduced pressure
  3. additionThe thus obtained residue was treated to a silica column chromatography (eluent: 3% methanol/dichloromethane)

Sources & evidence

ORD record
ord-7dd4d4ae66a24840abaace7d812fb2ea
Source dataset
uspto-grants-1999_12
Patent number
US05998437

Reaction notes

Loading…