Ammonium Chloride → 1-[2-(Morpholin-4-yl)ethyl]-1H-indazol-5-amine

HRID 1790120Notes

Reaction equation

HRID 1790120 reaction equation
[N:1]1([CH2:7][CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([N+:18]([O-])=O)=[CH:15][CH:16]=3)[CH:11]=[N:10]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl-].[NH4+]>[Fe].C(O)C.O>[N:1]1([CH2:7][CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([NH2:18])=[CH:15][CH:16]=3)[CH:11]=[N:10]2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 220365741-[2-(Morpholin-4-yl)ethyl]-5-nitro-1H-indazole

Product 1

HCID 574161351-[2-(Morpholin-4-yl)ethyl]-1H-indazol-5-amineYield 93%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 1-(2-morpholin-4-yl-ethyl)-5-nitro-1H-indazole (4.3 g, 16 mmol), iron powder (8.8 g, 157 mmol), and ammonium chloride (430 mg, 8 mmol) in a 4:1 ethanol/H2O solution (75 mL) 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, 50 mL) for 15 minutes, filtered through a plug of silica gel and rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under reduced pressure to provide the title compound (3.4 g, 93%). 1H NMR (300 MHz, DMSO-d6) ppm 2.40 (t, J=4.75, 4H), 2.70 (t, J=6.78, 2H), 3.50 (t, J=4.75, 4H), 4.38 (t, J=6.78, 2H), 4.78 (s, 2H), 6.72 (m, 1H), 6.80 (m, 1H), 7.35 (m, 1H), 7.60 (m, 1H); MS (DCI/NH3) m/z 247 [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
  5. washrinsed with triethylamine/ethyl acetate (1/4)
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-031ab4cec54c4ac7b7426df82ead85cd
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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