Ammonium Chloride → 3-chloro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamine

HRID 1790169Notes

Reaction equation

HRID 1790169 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[N:4]([CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[N:3]=1.[Cl-].[NH4+]>C(O)C.[Fe]>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[N:4]([CH2:14][CH2:15][N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[N:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 220365773-chloro-6-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole

Product 1

HCID 696526513-chloro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazol-6-ylamineYield 82.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-chloro-6-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (2.3 g, 7.8 mmol), iron powder (3.5 g, 62 mmol), and ammonium chloride (0.21 g, 3.9 mmol) in 80% Ethanol was heated to reflux for 3 hours, cooled to room temperature, and concentrated under reduced pressure. The residue was stirred in triethylamine/ethyl acetate (1/4, 20 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 (1.7 g, 80%). 1H NMR (300 MHz, DMSO-d6) ppm 1.64 (m, 4H), 2.45 (m, 4H), 2.78 (t, J=6.44, 2H), 4.21 (t, J=6.44, 2H), 5.56 (s, 2H), 6.48 (m, 1H), 6.58 (m, 1H), 7.25 (m, 1H); MS (DCI/NH3) m/z 265 [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-91125852705c46c2ac65ca624730bb73
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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