Ammonium Chloride → 2-(2-pyrrolidin-1-ylethyl)-2H-indazol-5-amine

HRID 1825825Notes

Reaction equation

HRID 1825825 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]2[C:6](=[CH:7][N:8]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[N:9]=2)[CH:5]=1)([O-])=O.[Cl-].[NH4+]>[Fe].C(O)C.O>[N:15]1([CH2:14][CH2:13][N:8]2[CH:7]=[C:6]3[C:10]([CH:11]=[CH:12][C:4]([NH2:1])=[CH:5]3)=[N:9]2)[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 221389045-Nitro-2-(2-(pyrrolidin-1-yl)ethyl)-2H-indazole

Product 1

HCID 112069772-(2-pyrrolidin-1-ylethyl)-2H-indazol-5-amine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 5-Nitro-2-(2-pyrrolidin-1-yl-ethyl)-2H-indazole (0.250 g, 0.961 mmol), iron powder (0.536 g, 9.60 mmol) and ammonium chloride (0.0257 g, 0.480 mmol) in a 4:1 ethanol/H2O solution was heated to reflux for 3 hours and then cooled to room temperature. The solvent was removed under vacuo and the residue stirred in triethylamine/ethyl acetate (1/4, 30 mL) for 15 minutes and then filtered through a plug of silica gel. After rinsing with triethylamine/ethyl acetate (1/4), the filtrate was concentrated unde vacuo to provide the title product. 1H NMR (300 MHz, DMSO-d6) ppm 1.79 (s, 4H), 2.48 (m, 4H), 2.88 (s, 2H), 3.26 (m, 2H), 4.58 (m, 2H), 6.57 (m, 1H), 6.76 (m, 1H), 7.34 (m, 1H), 7.96 (s, 1H); MS (DCI/NH3) m/z 231 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent was removed under vacuo
  4. filtrationfiltered through a plug of silica gel
  5. washAfter rinsing with triethylamine/ethyl acetate (1/4)
  6. concentrationthe filtrate was concentrated unde vacuo

Sources & evidence

ORD record
ord-0e40d2ea607c4b0e9418f776d704ced1
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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