Ammonium Chloride → 3-[2-(6-Amino-indazol-1-yl)-ethyl]-oxazolidin-2-one

HRID 1790153Notes

Reaction equation

HRID 1790153 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][O:17][C:16]2=[O:20])=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+]>[Fe].C(O)C.O>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][O:17][C:16]2=[O:20])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 220365783-[2-(6-Nitro-indazol-1-yl)-ethyl]-oxazolidin-2-one

Product 1

HCID 220365653-[2-(6-Amino-indazol-1-yl)-ethyl]-oxazolidin-2-oneYield 67.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

A mixture of 3-[2-(6-Nitro-indazol-1-yl)-ethyl]-oxazolidin-2-one (200 mg, 0.72 mmol), iron powder (400 mg, 7.1 mmol), and ammonium chloride (20 mg, 0.37 mmol) in a 4:1 ethanol/H2O solution (5 mL) was heated to reflux for 3 hours, cooled to room temperature, concentrated under reduced pressure. The resudue was stirred in triethylamine/ethyl acetate (1/4, 10 mL) for 15 minutes, filtered through a plug of silica gel which was rinsed with triethylamine/ethyl acetate (1/4). The filtrate was concentrated under reduced pressure to provide the title compound (120 mg, 67%). 1H NMR (300 MHz, DMSO-d6) ppm 4.03 (s, 3H), 4.42 (d, J=6.10, 1H), 6.04 (m, 1H), 7.25 (m, 1H), 7.32 (m, 1H), 7.38 (m, 1H), 7.48 (m, 2H), 7.69 (m, 1H), 7.79 (m, 1H), 8.44 (m, 1H), 9.12 (s, 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 which
  5. washwas rinsed with triethylamine/ethyl acetate (1/4)
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fb45ff45038845cc97d115942c5e8842
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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