Stannous Chloride → 4-(4-chloro-1H-1,2,3-triazol-1-yl)aniline

HRID 40736Notes

Reaction equation

HRID 40736 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=2)[CH:6]=1.Cl[Sn]Cl>C(O)C>[Cl:1][C:2]1[N:3]=[N:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 687732414-chloro-1-(4-nitrophenyl)-1H-1,2,3-triazole

Product 1

HCID 595880664-(4-chloro-1H-1,2,3-triazol-1-yl)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-chloro-1-(4-nitrophenyl)-1H-1,2,3-triazole (0.1 g, 0.45 mmol) in ethanol (3 mL) was added SnCl2 (0.4 g, 1.8 mmol) portionwise. The slurry was warmed up to 85° C. for 2.5 h, then quenched with NaOH (2M), filtered and concentrated. The residue was redissolved in EtOAc and washed with brine. The organic layer was separated, dried (MgSO4), and concentrated to afford 4-(4-chloro-1H-1,2,3-triazol-1-yl)aniline.

Workup

  1. customquenched with NaOH (2M)
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionThe residue was redissolved in EtOAc
  5. washwashed with brine
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-aa327e72d6a445cda4d6f8ffc6eb3592
Source dataset
uspto-grants-2013_09
Patent number
US08530480B2

Reaction notes

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