Hydrochloric Acid → 3-(2H-tetrazol-5-yl)-phenylamine hydrochloride

HRID 2399680Notes

Reaction equation

HRID 2399680 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[NH:14][N:13]=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[ClH:15]>C(O)C.[Pd]>[ClH:15].[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[NH:14][N:13]=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 2851295-(3-nitrophenyl)tetrazole

Product 1

HCID 212019913-(2H-tetrazol-5-yl)-phenylamine hydrochlorideYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-(3-nitrophenyl)tetrazole (22 g, 0.12 mol) in ethanol (500 mg) was added 10% palladium on carbon (1.5 g, 7% (w/w)) in hydrochloric acid (23 mg of a 5M solution). The mixture was hydrogenated at 40 psi for 10 min, then the catalyst filtered off and washed with water. The solvents were evaporated in vacuo and the brown solid azeotroped with toluene (4×100 mg). The resulting solid was triturated with hot ethanol to give 5-(3-aminophenyl)tetrazole hydrochloride (16.3 g, 71%) as a beige powder, mp 203°-205° C. 1H NMR (360 MHz, D2O) δ 7.63 (1H, d, J=9 Hz), 7.75 (1H, t, J=8 Hz), 8.00 (2H, m).

Workup

  1. filtrationthe catalyst filtered off
  2. washwashed with water
  3. customThe solvents were evaporated in vacuo
  4. customthe brown solid azeotroped with toluene (4×100 mg)
  5. customThe resulting solid was triturated with hot ethanol

Sources & evidence

ORD record
ord-ae2061ec10564ba0bcae4d1c8796c48c
Source dataset
uspto-grants-1995_09
Patent number
US05451582

Reaction notes

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