Nitrogen → HCID 66929203, compound

HRID 2064961Notes

Reaction equation

HRID 2064961 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[CH:13]=[C:12]([CH2:14][N:15]3[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[N:16]3)[O:11][N:10]=2)[O:8][CH2:7][CH2:6][O:5]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][C:4]1([C:9]2[CH:13]=[C:12]([CH2:14][N:15]3[CH:19]=[C:18]([NH2:20])[CH:17]=[N:16]3)[O:11][N:10]=2)[O:8][CH2:7][CH2:6][O:5]1

Participants

7

Reactant 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 66928768HCID 66928768, compound

Product 1

HCID 66929203HCID 66929203, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of 3-(2-methyl-[1,3]dioxolan-2-yl)-5-(4-nitro-pyrazol-1-ylmethyl)-isoxazole (150 mg, 0.54 mmol), iron powder (91 mg, 1.61 mmol) and NH4Cl (145 mg, 2.68 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 mL) was stirred at 85° C. for 20 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (20 mL) was added followed by water (20 mL). The aq. layer was extracted with CH2Cl2 (2×20 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a deep orange oil. LC-MS-conditions 02: tR=0.49 min; [M+H]+=251.34.

Workup

  1. filtrationThe reaction mixture was filtered while hot and
  2. concentrationconcentrated under reduced pressure
  3. additionCH2Cl2 (20 mL) was added
  4. extractionThe aq. layer was extracted with CH2Cl2 (2×20 mL)
  5. dry with materialextracts were dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-6b6e53aaa8674041b1298202966d5bf7
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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