4-(2H-1,2,3,4-tetrazol-2-yl)aniline → 4-(2H-Tetrazol-2-yl)phenol

HRID 1941510Notes

Reaction equation

HRID 1941510 reaction equation
[N:1]1[N:2]([C:6]2[CH:11]=[CH:10][C:9](N)=[CH:8][CH:7]=2)[N:3]=[N:4][CH:5]=1.N([O-])=[O:14].[Na+]>O.S(=O)(=O)(O)O.[Cl-].[Na+].O>[N:1]1[N:2]([C:6]2[CH:11]=[CH:10][C:9]([OH:14])=[CH:8][CH:7]=2)[N:3]=[N:4][CH:5]=1

Participants

6

Reactant 2

HCID 5716394-(2H-1,2,3,4-tetrazol-2-yl)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 157603994-(2H-Tetrazol-2-yl)phenolYield 29.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent4×HCID 1118Sulfuric AcidSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A suspension of 4-tetrazol-2-yl-phenylamine (5.4 g) in water (42 ml) and conc sulphuric acid (10 ml) was added slowly to a solution of sodium nitrite (2.3 g) in water (8.5 ml) at 5°. The resulting green solution was stirred at this temperature for ca. 30 min, treated with a mixture of water (50 ml) and conc. sulphuric acid (67 ml) and heated to 120° for 1 h. Water (170 ml) was added, the reaction mixture cooled, saturated with brine (100 ml) and extracted with dichloromethane (3×100 ml), dried (Na2SO4) and evaporated to give the title compound as an orange solid (1.6 g). T.l.c. (Ethyl acetate/cyclohexane (1:1)), Rf 0.55.

Workup

  1. temperatureheated to 120° for 1 h
  2. extractionextracted with dichloromethane (3×100 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-f8abc786f9d545f8b75b36581ffd3e5f
Source dataset
uspto-grants-1997_12
Patent number
US05703240

Reaction notes

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