1-t-Butoxycarbonyl-2,3-dihydro-7-methyl-6-nitroindole → 6-Amino-1-t-butoxycarbonyl-2,3-dihydro-7-methylindole

HRID 1275650Notes

Reaction equation

HRID 1275650 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:18]([O-])=O)[C:15]=2[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:18][C:14]1[C:15]([CH3:17])=[C:16]2[C:11]([CH2:10][CH2:9][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 158963701-t-Butoxycarbonyl-2,3-dihydro-7-methyl-6-nitroindole

Product 1

HCID 158963716-Amino-1-t-butoxycarbonyl-2,3-dihydro-7-methylindoleYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-t-Butoxycarbonyl-2,3-dihydro-7-methyl-6-nitroindole (0.58 g; 2.2 mmol) is dissolved in methanol (5 mL), treated with a catalytic amount of 10% palladium on carbon and placed under an atmosphere of hydrogen. The solution is allowed to stir overnight. The black suspension is filtered through Celite and the solvent is removed by rotary evaporation to afford 0.51 g of 6-amino-1-t-butoxycarbonyl-2,3-dihydro-7-methylindole as a white solid. (99% yield)

Workup

  1. filtrationThe black suspension is filtered through Celite
  2. customthe solvent is removed by rotary evaporation

Sources & evidence

ORD record
ord-7c62c82974624bbd9a80b4c786b25c34
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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