Ammonium Chloride → HCID 22138917, compound

HRID 1825822Notes

Reaction equation

HRID 1825822 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11]2)=[N:6]1.[Cl-].[NH4+]>[Fe].C(O)C.O>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([NH2:14])=[CH:11]2)=[N:6]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 2768024HCID 2768024, compound

Product 1

HCID 22138917HCID 22138917, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

Dimethyl-[2-(5-nitro-indazol-2-yl)-ethyl]-amine (0.300 g, 1.28 mmol), iron powder (0.715 g, 12.8 mmol) and ammonium chloride (0.0343 g, 0.641 mmol) was suspended in a 4:1 ethanol/H2O solution. The mixture was heated to reflux for 3 hours, cooled to room temperature and the solvents were removed under vacuo. The residue was stirred in triethylamine/ethyl acetate (1/4, 30 mL) for 15 minutes, filtered through a plug of silica gel followed by rinsing with triethylamine/ethyl acetate (1/4). The filtrate was concentrated to provide the titled product. 1H NMR (300 MHz, DMSO-d6) ppm 2.16 (s, 6H) 2.72 (t, 2H, J=6.44), 4.35 (t, 2H, J=6.44), 4.74 (s, 2H), 6.55 (dm, 1H), 6.72 (m, 1H), 7.30 (m, 1H), 7.89 (s, 1H); MS (DCI/NH3) m/z 205 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customthe solvents were removed under vacuo
  4. filtrationfiltered through a plug of silica gel
  5. washby rinsing with triethylamine/ethyl acetate (1/4)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-11afb041e47d47afa6c9a92b9d06ecc8
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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