2-{2-[3-(1H-Indol-3-yl)-propylamino]-ethoxy}-6-nitro-phenylamine → 3-{2-[3-(1H-Indol-3-yl)-propylamino]-ethoxy}-benzene-1,2-diamine

HRID 1858361Notes

Reaction equation

HRID 1858361 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-])=O)[C:18]=2[NH2:26])=[CH:2]1>C(O)C.[Pd]>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[C:18]=2[NH2:26])=[CH:2]1

Participants

4

Reactant 1

HCID 114736902-{2-[3-(1H-Indol-3-yl)-propylamino]-ethoxy}-6-nitro-phenylamine

Product 1

HCID 112442363-{2-[3-(1H-Indol-3-yl)-propylamino]-ethoxy}-benzene-1,2-diamineYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the 2-{2-[3-(1H-indol-3-yl)-propylamino]-ethoxy}-6-nitro-phenylamine (1.9 g, 5.39 mmol) in ethanol (40 ml) was added 5% palladium on carbon (0.5 g) under nitrogen. The resulting slurry was hydrogenated under 40 psi for 4 hours. The catalyst was removed by filtration and the ethanol evaporated to afford the crude product. Purification by chromatography (3-10% 2N ammonia methanol in methylene chloride) gave 1.57 g (90.6%) of product as a brown oil. 1H NMR (400 MHZ, DMSO-d6), δ1.79, (2H, q, J=7.2 Hz); 2.62, (2H, t, J=7.1 Hz); 2.71, (2H, t, J=7.2 Hz); 2.83, (2H, t, J=5.2 Hz); 4.09, (2H, br); 4.43, (2H, br); 6.19, (1H, t, J=8.0 Hz); 6.33, (1H, t, J=7.9 Hz); 6.94; (1H, t, J=7.0 Hz); 7.03, (1H, t, J=7.2 Hz); 7.08, (1H, d, J=2.0 Hz); 7.29, (2H, d, J=7.4 Hz); 7.31, (2H, d, J=7.4 Hz); 10.7, (1H, br).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe ethanol evaporated
  3. customto afford the crude product
  4. customPurification by chromatography (3-10% 2N ammonia methanol in methylene chloride)

Sources & evidence

ORD record
ord-f9777165173046ec9ad347499cfd334b
Source dataset
uspto-grants-2000_11
Patent number
US06150533

Reaction notes

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