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

HRID 1419173Notes

Reaction equation

HRID 1419173 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=2)[NH:7][CH:6]=1>[Pd].C(O)C>[NH2:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH3:17]

Participants

4

Reactant 1

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

Product 1

HCID 118202113-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLAMINEYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-(2-dimethylaminoethyl)-5-nitroindole (1.85 g, 7.93 mmol) and 10% palladium on carbon (0.40 g, 20% by weight) in absolute ethanol (30 mL) was shaken under a hydrogen atmosphere (3 atm) for 6 hours. The resulting mixture was filtered through Celite®, and the Celite® pad was washed generously with absolute ethanol. The combined filtrates were evaporated under reduced pressure to afford the title compound (1.60 g, 7.87 mmol, 99%) as a clear, slightly dark, hygroscopic oil: IR (CHCl3) 3480, 1610, 1585, 1460, 1335 cm-1 ; 1H NMR (CDCl3) δ 8.10 (br m, NH), 7.12 (d, J=8.5 Hz, 1H), 6.91 (d, J=2.3 Hz, 1H), 6.88 (d, J=2.2 Hz, 1H), 6.64 (dd, j=2.2 and 8.5 Hz, 1H), 2.89-2.84 (m, 2H), 2.64-2.58 (m, 2H), 2.34 (s, 6H); 13C NMR (CDCl3) δ 139.1, 131.2, 128.3, 122.2, 113.1, 112.9, 111.7, 103.8, 60.3, 45.4, 23.7; LRMS (m/z, relative intensity) 203 (9, M+), 158 (2), 145 (6), 83 (66), 58 (100). HRMS calculated for C12H17N3 203.1424, found 203.1418. Anal. calcd for C12H17N3.1/2 H2O: C, 67.89; H, 8.55; N, 19.79. Found: C, 67.71; H, 8.60; N, 19.41.

Workup

  1. filtrationThe resulting mixture was filtered through Celite®
  2. washthe Celite® pad was washed generously with absolute ethanol
  3. customThe combined filtrates were evaporated under reduced pressure

Sources & evidence

ORD record
ord-318cab52a01d46b19013f3537b08dd27
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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