2-cyclohexyl-1-ethyl-5-nitro-1H-indole → 2-cyclohexyl-1-ethyl-1H-indol-5-amine

HRID 1947434Notes

Reaction equation

HRID 1947434 reaction equation
[CH:1]1([C:7]2[N:8]([CH2:19][CH3:20])[C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([N+:16]([O-])=O)=[CH:11][CH:10]=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C(O)C>[CH:1]1([C:7]2[N:8]([CH2:19][CH3:20])[C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([NH2:16])=[CH:11][CH:10]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 672850022-cyclohexyl-1-ethyl-5-nitro-1H-indole

Product 1

HCID 672845702-cyclohexyl-1-ethyl-1H-indol-5-amineYield 91.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a suspension of 10% Pd/C (380 mg, 0.36 mmol) in 95° ethanol (50 ml) a solution of 2-cyclohexyl-1-ethyl-5-nitro-1H-indole (4.8 g; 18 mmol) in 95° ethanol (100 ml) was added and the mixture underwent hydrogenation in a Parr hydrogenator (H2, 30 psi) for 4 hours. The residue was filtered under vacuum through Celite to remove the catalyst and the solvent evaporated to give crude 2-cyclohexyl-1-ethyl-1H-indol-5-amine (4 g) which was used without any further purification.

Workup

  1. additionwas added
  2. filtrationThe residue was filtered under vacuum through Celite
  3. customto remove the catalyst
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-42065b700b2040ae9ead90ef3ec11dd2
Source dataset
uspto-grants-2013_03
Patent number
US08399477B2

Reaction notes

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