Ammonium Chloride → HCID 11401973, compound

HRID 1825816Notes

Reaction equation

HRID 1825816 reaction equation
[N+:1]([C:4]1[C:5]2[C:9]([CH:10]=[CH:11][CH:12]=1)=[N:8][N:7]([CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[CH:6]=2)([O-])=O.[Cl-].[NH4+]>[Fe].C(O)C.O>[N:15]1([CH2:14][CH2:13][N:7]2[CH:6]=[C:5]3[C:9]([CH:10]=[CH:11][CH:12]=[C:4]3[NH2:1])=[N:8]2)[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 22138912HCID 22138912, compound

Product 1

HCID 11401973HCID 11401973, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

4-Nitro-2-(2-pyrrolidin-1-yl-ethyl)-2H-indazole (1.20 g, 4.62 mmol), iron powder (2.60 g, 46.6 mmol) and ammonium chloride (0.125 g, 2.34 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 solvent removed in vacuo. The residue was stirred in triethylamine/ethyl acetate (1/4, 30 mL) for 15 minutes and 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) δ ppm 1.66 (m, 4H), 2.50 (m, 4H), 2.96 (t, 2H, J=6.44), 4.44 (t, 2H, J=6.44), 5.51 (s, 2H), 6.70 (m, 1H), 6.88 (d, 1H, J=8.48), 6.91 (m, 1H), 8.28 (s, 1H); MS (DCI/NH3) m/z 231 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customthe solvent 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-68c0d9e92775421094ab923672905cb9
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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