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

HRID 440793

Reaktionsgleichung

Reaktionsgleichung von HRID 440793
[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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-27e268d3d17d470094805b5f3ae5e61e
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521175

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