5-nitro-1-(2-pyrrolidin-1-ylethyl)-1H-indole → 5-Amino-1-(2-pyrrolidin-1-ylethyl)indole

HRID 601513Notes

Reaction equation

HRID 601513 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH:8]=[CH:7]2)([O-])=O>C(O)C.[Pd]>[N:15]1([CH2:14][CH2:13][N:9]2[C:10]3[C:6](=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=3)[CH:7]=[CH:8]2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 1

HCID 114026955-nitro-1-(2-pyrrolidin-1-ylethyl)-1H-indole

Product 1

HCID 113905745-Amino-1-(2-pyrrolidin-1-ylethyl)indole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve 5-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indole (375 mg, 1.45 mmol) in ethanol (15 mL) and add 5% Pd/C (149 mg). Purge the black mixture with hydrogen (1 atm) and stir overnight under a hydrogen atmosphere. Filter the black mixture through Celite® and wash the solids with additional ethanol (˜10 mL). Concentrate the filtrate to give the title compound as a yellow solid. MS (ES+) 230.2 (M+1)+. 1H NMR (400 MHz, CDCl3): δ: 7.17 (d, 1H, J=8.8 Hz), 7.05 (d, 1H, J=3.1 Hz), 6.92 (d, 1H, J=2.2 Hz), 6.67 (dd, 1H, J=8.3, 2.2 Hz), 6.29 (d, 1H, J=3.1 Hz), 4.21 (t, 2H, J=7.5 Hz), 3.37 (s, 2H), 2.86 (t, 2H, J=7.5 Hz), 2.55 (m, 4H), 1.79 (m, 4H).

Workup

  1. customPurge the black mixture with hydrogen (1 atm)
  2. filtrationFilter the black mixture through Celite®
  3. washwash the solids with additional ethanol (˜10 mL)
  4. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-dc0bc54a9d7b4814828cd6fc23a8d9ef
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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