Nitrogen → HCID 66929216, compound

HRID 2064976Notes

Reaction equation

HRID 2064976 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH2:15][N:16]3[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[N:17]3)[CH:14]=2)[O:8][CH2:7][CH2:6][O:5]1.[NH4+].[Cl-]>CCO.O.[Fe]>[CH3:3][C:4]1([C:9]2[CH:14]=[C:13]([CH2:15][N:16]3[CH:20]=[C:19]([NH2:21])[CH:18]=[N:17]3)[CH:12]=[N:11][CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1

Participants

7

Reactant 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 66928958HCID 66928958, compound

Product 1

HCID 66929216HCID 66929216, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a 0.1M solution of 3-(2-methyl-[1,3]dioxolan-2-yl)-5-(4-nitro-pyrazol-1-ylmethyl)-pyridine (40 mg, 0.14 mmol), iron powder (23 mg, 0.41 mmol) and NH4Cl (37 mg, 0.69 mmol) in a mixture of EtOH (4.0 mL) and water (2.0 mL) was stirred at 75° C. for 30 min. The reaction mixture was filtered while hot and concentrated under reduced pressure. CH2Cl2 (20 mL) was added followed by 1N NaOH (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 red oil. TLC: rf (50:50 hept-EA)=0.1. LC-MS-conditions 02: tR=0.35 min; [M+H]+=261.29.

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-413de6a02369464cba16f3f18f8f5848
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

Loading…