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

HRID 440793Notes

Reaction equation

HRID 440793 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 ml) was added 10% palladium on carbon (1.5 g, 7% (w/w)) in hydrochloric acid (23 ml 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 ml). 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.; δH (360 MHz, D2O) 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 ml)
  5. customThe resulting solid was triturated with hot ethanol

Sources & evidence

ORD record
ord-27e268d3d17d470094805b5f3ae5e61e
Source dataset
uspto-grants-1996_05
Patent number
US05521175

Reaction notes

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