Ammonium Chloride → HCID 22138919, compound

HRID 1825835Notes

Reaction equation

HRID 1825835 reaction equation
[CH3:1][O:2][CH:3]([O:17][CH3:18])[CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([N+:14]([O-])=O)[CH:10]=[CH:11]2)=[N:6]1.[NH4+].[Cl-]>C(O)C.O.[Fe]>[CH3:18][O:17][CH:3]([O:2][CH3:1])[CH2:4][N:5]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([NH2:14])[CH:10]=[CH:11]2)=[N:6]1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 22138907HCID 22138907, compound

Product 1

HCID 22138919HCID 22138919, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

To a stirred solution of 2-(2,2-dimethoxyethyl)-6-nitro-2H-indazole (1.89 g, 7.52 mmol) and NH4Cl (337 mg, 6.01 mmol) in ethanol/H2O (2:1, 75 mL) at room temperature was added Fe (1.28 g, 23.7 mmol) and the resulting mixture was heated for 2 hours at 70 C. The mixture was allowed to cool and was filtered through celite. The residue was washed with hot Methanol (5×20 mL) and the combined eluent was concentrated under reduced pressure. The residue was diluted with ethyl acetate (50 mL) and filtered. Concentration of the organic layer under reduced pressure provided 2-(2,2-dimethoxyethyl)-2H-indazol-6-ylamine as an amber oil. 1H NMR (300 MHz, DMSO-d6) δ ppm 3.25 (m, 6 H), 4.34 (d, J=5.43 Hz, 2 H), 4.81 (t, J=5.59 Hz, 1 H), 5.22 (s, 2 H), 6.52 (m, 2 H), 7.37 (m, 1 H) and 8.02 (s, 1 H); MS (ESI) 222 (M+H)+.

Workup

  1. temperaturethe resulting mixture was heated for 2 hours at 70 C
  2. temperatureto cool
  3. filtrationwas filtered through celite
  4. washThe residue was washed with hot Methanol (5×20 mL)
  5. concentrationthe combined eluent was concentrated under reduced pressure
  6. additionThe residue was diluted with ethyl acetate (50 mL)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-586c36bbe44c404dbd554c25cab07f62
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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