Ammonium Chloride → HCID 22138910, compound

HRID 1825833Notes

Reaction equation

HRID 1825833 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+]([O-])=O)=[CH:11]2)=[N:6]1.[Cl-].[NH4+:19].[CH2:20](O)[CH3:21].O>[Fe]>[N:2]1([CH2:3][CH2:4][N:5]2[CH:13]=[C:12]3[C:7]([CH:8]=[C:9]([NH2:19])[CH:10]=[CH:11]3)=[N:6]2)[CH2:17][CH2:21][CH2:20][CH2:1]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2768024HCID 2768024, compoundHCID 19096565Water ethanol

Product 1

HCID 22138910HCID 22138910, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Dimethyl-[2-(5-nitro-indazol-2-yl)-ethyl]-amine (0.275 g, 1.17 mmol), iron powder (0.656 g, 11.7 mmol) and ammonium chloride (0.0314 g, 0.587 mmol) was suspended in a 4:1 ethanol/H2O solution. The reaction mixture was heated to reflux for 3 hours and then cooled to room temperature. The solvent was removed in 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 to provide the title product. 1H NMR (300 MHz, DMSO-d6) ppm 2.16 (s, 6H), 2.71 (t, 2H, J=6.44), 4.31 (t, 2H, J=6.44), 4.98 (s, 2H), 6.46 (m, 1H), 6.50 (m, 1H), 7.33 (s, 1H), 8.03 (s, 1H); MS (DCI/NH3) m/z 205 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-368a7ec8dc3c4a90a8bd6e530c39f8ec
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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