1-Acetyl-5-(2-azidopropyl)indoline-7-carbonitrile → 1-Acetyl-5-(2-aminopropyl)-2,3-dihydro-1H-indole-7-carbonitrile

HRID 273846Notes

Reaction equation

HRID 273846 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH:16]([N:18]=[N+]=[N-])[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>C(O)C.[Pd]>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH:16]([NH2:18])[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 200943521-Acetyl-5-(2-azidopropyl)indoline-7-carbonitrile

Product 1

HCID 200943331-Acetyl-5-(2-aminopropyl)-2,3-dihydro-1H-indole-7-carbonitrileYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-acetyl-5-(2-azidopropyl)indoline-7-carbonitrile (0.20 g) in ethanol (16 ml) was added 5% palladium on barium sulfate (102 mg), and the mixture was stirred at room temperature for 8 hours under an atmosphere of hydrogen. After the catalyst was filtered off, the filtrate was concentrated to dryness to give 0.18 g of 1-acetyl-5-(2-aminopropyl)indoline-7-carbonitrile melting at 94°-96° C.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-e97df301263b43e5aaffc58c3cd1bb44
Source dataset
uspto-grants-1995_02
Patent number
US05387603

Reaction notes

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