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

HRID 2037944Notes

Reaction equation

HRID 2037944 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+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-fb54b4b13a17402a84667abc20c08ffc
Source dataset
uspto-grants-2013_11
Patent number
US08575209B2

Reaction notes

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