Nitrogen → 2-[4-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl]-2H-[1,2,3]triazol-4-ylamine

HRID 42780Notes

Reaction equation

HRID 42780 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[N: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[N: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 673638394-(2-Methyl-[1,3]dioxolan-2-yl)-2-(4-nitro-[1,2,3]triazol-2-ylmethyl)-pyridine

Product 1

HCID 673651922-[4-(2-Methyl-[1,3]dioxolan-2-yl)-pyridin-2-ylmethyl]-2H-[1,2,3]triazol-4-ylamine

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-[1,2,3]triazol-2-ylmethyl)-pyridine (210 mg, 0.71 mmol), iron powder (120 mg, 2.12 mmol) and NH4Cl (191 mg, 3.53 mmol) in a mixture of EtOH (2.0 mL) and water (1.0 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. Purification of the residue by FC (99:1 to 19:1 CH2Cl2-MeOH) gave the title compound as a brown oil: TLC:rf (19:1 CH2Cl2-MeOH)=0.33. LC-MS: tR=0.64 min, [M+H]+=262.29.

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
  9. customPurification of the residue by FC (99:1 to 19:1 CH2Cl2-MeOH)

Sources & evidence

ORD record
ord-5dc9d0ccf24a4d0cb69f7af87132726a
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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