3-methyl-6-nitro-1H-indole → HCID 18916040, compound

HRID 2404650Notes

Reaction equation

HRID 2404650 reaction equation
CC1C2C(=CC=CC=2[N+]([O-])=O)NC=1.[CH3:14][C:15]1[C:23]2[C:18](=[CH:19][C:20]([N+:24]([O-])=O)=[CH:21][CH:22]=2)[NH:17][CH:16]=1>C(O)C.[Pd]>[CH3:14][C:15]1[C:23]2[C:18](=[CH:19][C:20]([NH2:24])=[CH:21][CH:22]=2)[NH:17][CH:16]=1

Participants

5

Reactant 2

HCID 33588543-methyl-6-nitro-1H-indoleHCID 3807122HCID 3807122, compound

Product 1

HCID 18916040HCID 18916040, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-methyl-4-nitro-1H-indole and 3-methyl-6-nitro-1H-indole (3 g, 17 mol) and 10% Pd—C (0.5 g) in ethanol (30 mL) was stirred overnight under H2 (1 atm) at room temperature. Pd—C was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography to give 3-methyl-1H-indol-6-ylamine (B-7) (0.6 g, 24%). 1H NMR (CDCl3) δ 7.59 (br s, 1H), 7.34 (d, J=8.0 Hz, 1H), 6.77 (s, 1H), 6.64 (s, 1H), 6.57 (m, 1H), 3.57 (br s, 2H), 2.28 (s, 3H); ESI-MS 147.2 m/z (MH+).

Workup

  1. filtrationPd—C was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-459bad546ac04c2aa07a12de263d0798
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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