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

HRID 1790115Notes

Reaction equation

HRID 1790115 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=2)[CH:7]=[N:6]1.[Cl-].[NH4+]>[Fe].C(O)C.O>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[CH:7]=[N:6]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 2157401H-Indazole-1-ethanamine, N,N-dimethyl-5-nitro-

Product 1

HCID 696529021-(2-dimethylamino-ethyl)-1H-indazol-5-ylamineYield 92%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of dimethyl-[2-(5-nitro-indazol-1-yl)-ethyl]-amine (1 g, 4.3 mmol), iron powder (1.9 g, 34 mmol), and ammonium chloride (120 mg, 2.2 mmol) in a 4:1 ethanol/H2O solution (20 mL) 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, 10 mL) for 15 minutes and then 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 (0.80 g, 92%). 1H NMR (300 MHz, DMSO-d6) ppm 2.15 (s, 6H), 2.64 (t, J=6.44, 2H), 4.34 (t, J=6.44, 2H), 4.77 (s, 2H), 6.72 (m, 1H), 6.79 (m, 1H), 7.35 (m, 1H), 7.67 (m, 1H); MS (DCI/NH3) m/z 205 [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-ab0730f109964f06a3623f53a593e2b4
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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