Nitrogen → HCID 66929128, compound

HRID 2064995Notes

Reaction equation

HRID 2064995 reaction equation
N#N.[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18](=[O:20])[CH3:19])[CH:13]=2)[CH:10]=1)([O-])=O.[NH4+].[Cl-]>CCO.O.[Fe]>[NH2:3][C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18](=[O:20])[CH3:19])[CH:13]=2)[CH:10]=1

Participants

7

Reactant 3

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 66928652HCID 66928652, compound

Product 1

HCID 66929128HCID 66929128, 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 1-[4-(4-nitro-pyrazol-1-ylmethyl)-pyridin-2-yl]-ethanone (250 mg, 1.01 mmol), iron powder (172 mg, 3.05 mmol) and NH4Cl (274 mg, 5.08 mmol) in a mixture of EtOH (4.0 mL) and water (2.0 mL) was stirred at 75° C. for 5 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 brown oil. TLC: rf (1:2 hept-EA)=0.05. LC-MS-conditions 02: tR=0.50 min, [M+H]+=217.47.

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-5eff5b1fa8b84695963c9acef1b8639c
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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