Ammonium Chloride → 1-(2-Pyrrolidin-1-YL-ethyl)-1H-indazol-4-ylamine

HRID 1790083Notes

Reaction equation

HRID 1790083 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)([O-])=O.[Cl-].[NH4+]>[Fe].C(O)C.O>[N:15]1([CH2:14][CH2:13][N:8]2[C:9]3[C:5](=[C:4]([NH2:1])[CH:12]=[CH:11][CH:10]=3)[CH:6]=[N:7]2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 220365874-nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole

Product 1

HCID 114923411-(2-Pyrrolidin-1-YL-ethyl)-1H-indazol-4-ylamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

4-Nitro-1-(2-pyrrolidin-1-yl-ethyl)-1H-indazole (1.90 g, 7.30 mmol), iron powder (4.10 g, 73.4 mmol), and ammonium chloride (0.200 g, 3.65 mmol) were suspended in a 4:1 solution of ethanol/H2O. The mixture was heated to reflux for 3 hours, cooled to room temperature and concentrated under reduced pressure. The residue was taken up and stirred in triethylamine/ethyl acetate (1/4, 30 mL) for 15 minutes and filtered through a plug of silica gel. The silica gel was rinsing with triethylamine/ethyl acetate (1/4) and combined filtrate concentrated under reduced pressure to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.62 (m, 4H), 2.44 (m, 4H), 2.81 (t, 2H, J=6.78), 4.34 (t, 2H, J=6.78), 5.73 (s, 2H), 6.13 (m, 1H), 6.66 (m, 1H), 7.01 (m, 1H), 8.05 (s, 1H); MS (DCI/NH3) m/z 231 [M+H]+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. filtrationfiltered through a plug of silica gel
  5. washThe silica gel was rinsing with triethylamine/ethyl acetate (1/4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-232bffef5bf8497b9ca109bcf832a45f
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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