6-Nitro-1H-indole → 6-Aminoindole

HRID 358735Notes

Reaction equation

HRID 358735 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-reduced 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-8b5461613c734c1ea78b727b32a31b45
Source dataset
uspto-grants-1991_03
Patent number
US04997844

Reaction notes

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