6-Nitro-1H-indole → 6-Aminoindole

HRID 2254177Notes

Reaction equation

HRID 2254177 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 785026-Nitro-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 2560966-Aminoindole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A yellow solution of 5.2 g. 6-nitroindole in 150 ml. ethyl acetate was added to 1.25 g. of pre-induced 10% w/w palladium-on-charcoal in 50 ml. ethyl acetate. The mixture was shaken under 3.45 bar hydrogen overnight and then filtered through diatomaceous earth. The residue was washed with 150 ml. hot chloroform and the combined colourless filtrate and washings were evaporated to give a quantitative yield of 6-aminoindole as a dark oil; NMR: 3.5 (br s, 2H, NH2), 6.4 (m, 1H, H3). 6.5 (m, 2H, H5 +H7), 7.0 (dd, 1H, H2, 7.4 (d, 1H, H4), 7.8 (br, 1H, NH).

Workup

  1. filtrationfiltered through diatomaceous earth
  2. washThe residue was washed with 150 ml
  3. customhot chloroform and the combined colourless filtrate and washings were evaporated

Sources & evidence

ORD record
ord-eaafb538597c4246a869562785facd29
Source dataset
uspto-grants-1993_08
Patent number
US05234942

Reaction notes

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