HCID 59129442, compound → 2-Cyclopropyl-1H-indol-5-amine

HRID 1403902Notes

Reaction equation

HRID 1403902 reaction equation
[CH:1]1([C:4]2[NH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][C:9]([N+:13]([O-])=O)=[CH:8][CH:7]=3)[CH2:3][CH2:2]1>CO.[Ni]>[CH:1]1([C:4]2[NH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][C:9]([NH2:13])=[CH:8][CH:7]=3)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 59129442HCID 59129442, compound

Product 1

HCID 591293002-Cyclopropyl-1H-indol-5-amineYield 56%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-cyclopropyl-5-nitro-1H-indole (1.3 g, 6.4 mmol) in MeOH (30 mL) was added Raney Nickel (0.3 g) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered through a Celite pad and the filtrate was evaporated under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to give 2-cyclopropyl-1H-indol-5-amine (510 mg, 56%). 1H NMR (400 MHz, CDCl3) δ 6.89 (d, J=8.4 Hz, 1H), 6.50 (d, J=1.6 Hz, 1H), 6.33 (dd, J=2.0, 8.4 Hz, 1H), 5.76 (s, 1H), 4.33 (brs, 2H), 1.91-1.87 (m, 1H), 0.90-0.85 (m, 2H), 0.70-0.66 (m, 2H); MS (ESI) m/e (M−1-H+) 173.2.

Workup

  1. filtrationThe catalyst was filtered through a Celite pad
  2. customthe filtrate was evaporated under vacuum
  3. customto give the crude product, which
  4. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-947fc6a209b3490ea8603761cd0519ea
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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