3-(2'-Methyl-2'-nitrobutyl)-indole → 3-(2'-Amino-2'-methylbutyl)-indole

HRID 268459

Reaction equation

HRID 268459 reaction equation
[CH3:1][C:2]([N+:15]([O-])=O)([CH2:13][CH3:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[H][H]>[Pd].C(O)C>[NH2:15][C:2]([CH3:1])([CH2:13][CH3:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

5

Reactant 2

HCID 215522423-(2'-Methyl-2'-nitrobutyl)-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 215522353-(2'-Amino-2'-methylbutyl)-indoleYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Reduction: A mixture of 90.0 g (388 mM) of the nitro intermediate and 9.0 g of palladium catalyst (5% on carbon) and 1000 ml of absolute ethanol was covered with hydrogen at a pressure of 25 atmospheres gauge in the autoclave whereupon it was heated to 70°C. and agitation was continued at this temperature for 7 hours. Filtration, evaporation in vacuo, recrystallisation from xylene and processing of the mother liquor yielded 74.7 g of 3-(2'-amino-2'-methylbutyl)-indole. (Yield: 95% of the theoretical).

Workup

  1. filtrationFiltration, evaporation
  2. customin vacuo, recrystallisation from xylene and processing of the mother liquor

Sources & evidence

ORD record
ord-1967a7e4e7cb4c268178129f7030ca79
Source dataset
uspto-grants-1976_03
Patent number
US03947584

Linked notes

Loading…