3-(2-DIMETHYLAMINOETHYL)-5-NITROINDOLE → 3-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLAMINE

HRID 1769639Notes

Reaction equation

HRID 1769639 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][N:15]([CH3:16])[CH3:17]

Participants

4

Reactant 1

HCID 9499653-(2-DIMETHYLAMINOETHYL)-5-NITROINDOLE

Product 1

HCID 118202113-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLAMINEYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-nitro-3-[2-(dimethylamino) ethyl]indole (0.650 g, 2.79 mmol) and 10% palladium-on-charcoal (0.150 g) in 60 mL of ethanol was hydrogenated on a Parr shaker at 40 psi for 30 min. The mixture was then filtered through Celite and the catalyst was washed with additional ethanol. Evaporation of the filtrate gave the essentially pure title compound (0.510 g, 90%) as a light brown gum: IR (neat) 3410, 1630, 1588, 1464 cm-1 ; 1H NMR (CDCl3, 200 MHz) δ7.84 (br s, 1H), 7.15 (d, J=8.5 Hz, 1H), 6.94 (d, J=2.2 Hz, 1H), 6.90 (d, J=2.1 Hz, 1H), 6.66 (dd, J=8.5, 2.2 Hz, 1H), 3.44 (br s, 2H), 2.88 (m, 2H), 2.60 (m, 2H), 2.34 (s, 6H).

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. washthe catalyst was washed with additional ethanol
  3. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-8750cf8b40714857a6244bc1e771adc8
Source dataset
uspto-grants-1995_01
Patent number
US05382592

Reaction notes

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