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

HRID 541075Notes

Reaction equation

HRID 541075 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-e242bc37a01e4cffb2a07965a5af6638
Source dataset
uspto-grants-2014_10
Patent number
US08871948B2

Reaction notes

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