Sodium Hydroxide → 3-(2-Methyl-2H-tetrazol-5-yl)aniline

HRID 1633952Notes

Reaction equation

HRID 1633952 reaction equation
[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=2)=[N:3]1.[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[N:6]=[N:5][C:4]([C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=2)[NH2:13])=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 140450862-Methyl-5-(3-nitrophenyl)-2H-tetrazole

Product 1

HCID 144421273-(2-Methyl-2H-tetrazol-5-yl)aniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-5-(3-nitrophenyl)-2H-tetrazole (2.12 g, 10 mmol) was added ethanol (50 mL) and heated to reflux. At reflux, the mixture was added SnCl2 dihydrate (11.6 g, 52 mmol) and the mixture was heated at reflux for 2 hours. After cooling, the mixture was poured into ice/water (200 mL) and neutralised (to pH 7) with 1 N sodium hydroxide. The mixture was filtered through celite, and the filter cake was washed with ethyl acetate. For the combined filtrate and washings the phases were separated and the aqueous phase was extracted with ethyl acetate (2×250 mL). The combined organic phases were dried (MgSO4) and evaporated in vacuo to afford 3-(2-methyl-2H-tetrazol-5-yl)aniline.

Workup

  1. temperatureheated to reflux
  2. temperatureAt reflux
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 2 hours
  5. temperatureAfter cooling
  6. filtrationThe mixture was filtered through celite
  7. washthe filter cake was washed with ethyl acetate
  8. customFor the combined filtrate and washings the phases were separated
  9. extractionthe aqueous phase was extracted with ethyl acetate (2×250 mL)
  10. dry with materialThe combined organic phases were dried (MgSO4)
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-afdb4265a04b464c8bf571365248cf4d
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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