Nitrogen → HCID 66928657, compound

HRID 2064989Notes

Reaction equation

HRID 2064989 reaction equation
N#N.[CH3:3][C:4]1([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([CH2:15][N:16]3[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[N:17]3)[CH: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:14]=[CH:13][N:12]=[C:11]([CH2:15][N:16]3[CH:20]=[C:19]([NH2:21])[CH:18]=[N:17]3)[CH:10]=2)[O:8][CH2:7][CH2:6][O:5]1

Participants

7

Reactant 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 66928750HCID 66928750, compound

Product 1

HCID 66928657HCID 66928657, 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 mixture of 4-(2-methyl-[1,3]dioxolan-2-yl)-2-(4-nitro-pyrazol-1-ylmethyl)-pyridine (174 mg, 0.60 mmol), iron powder (101 mg, 1.80 mmol) and NH4Cl (162 mg, 3.00 mmol) in a mixture of EtOH (4.0 mL) and water (2.0 mL) was stirred at 75° C. for 1 h. The reaction mixture was filtered while hot and the filter cake rinsed with EtOH. The filtrate was concentrated under reduced pressure and the residue partitioned between CH2Cl2 (10 mL) and aq. 1M NaOH (10 mL). The aq. layer was extracted with CH2Cl2 (2×10 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvent removed under reduced pressure to give the title compound as a red oil. LC-MS-conditions 02: tR=0.55 min, [M+H]+=261.39.

Workup

  1. filtrationThe reaction mixture was filtered while hot and the filter cake
  2. washrinsed with EtOH
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue partitioned between CH2Cl2 (10 mL) and aq. 1M NaOH (10 mL)
  5. extractionThe aq. layer was extracted with CH2Cl2 (2×10 mL)
  6. dry with materialextracts were dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-62d909712efe47d2ba73ecb91e86c0c1
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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