Ammonium Chloride → 1-(2-Pyrrolidin-1-YL-ethyl)-1H-indazol-5-ylamine

HRID 1790102Notes

Reaction equation

HRID 1790102 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)[N:8]=[CH:7]2)([O-])=O.[Cl-].[NH4+]>[Fe].C(O)C.O>[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]=[N:8]2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 220365795-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole

Product 1

HCID 113107771-(2-Pyrrolidin-1-YL-ethyl)-1H-indazol-5-ylamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 5-Nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (3.00 g, 11.5 mmol), iron powder (6.50 g, 116 mmol), and ammonium chloride (310 mg, 5.85 mmol) in a 4:1 mixture of ethanol/H2O was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was taken up and stirred in triethylamine/ethyl acetate (1/4, 30 mL) for 15 minutes, filtered through a plug of silica gel which was rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.62 (m, 4H), 2.44 (m, 4H), 2.81 (t, 2H, J=6.78), 4.36 (t, 2H, J=6.78), 4.77 (s, 2H), 6.72 (m, 1H), 6.79 (m, 1H), 7.35 (m, 1H), 7.68 (s, 1H); MS (DCI/NH3) m/z 231 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered through a plug of silica gel which
  5. washwas rinsed with triethylamine/ethyl acetate (1/4)
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5db7914aba2741b29ed80ae6060453c2
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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