1-(3-nitrophenyl)-1H-tetrazol-5-ol → 1-(3-aminophenyl)-1,4-dihydro-5H-tetrazol-5-one

HRID 59047Notes

Reaction equation

HRID 59047 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[NH:13][N:12]=[N:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[NH:13][N:12]=[N:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 1360089101-(3-nitrophenyl)-1H-tetrazol-5-ol

Product 1

HCID 1360622141-(3-aminophenyl)-1,4-dihydro-5H-tetrazol-5-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(3-nitrophenyl)-1,4-dihydro-5H-tetrazol-5-one (130 mg, 0.63 mmol) and palladium on charcoal (Aldrich Cat. No. 330108; 13 mg) in MeOH (10 mL) was hydrogenated at 20 psi for 3 hr. The mixture was then filtered through celite and the filter cake washed with MeOH (×3). The filtrate was concentrated under vacuum to leave the product, which was used directly in the next step (yield assumed quantitative=111 mg).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washthe filter cake washed with MeOH (×3)
  3. concentrationThe filtrate was concentrated under vacuum
  4. customto leave the product, which
  5. customwas used directly in the next step (yield assumed quantitative=111 mg)

Sources & evidence

ORD record
ord-2816d3e285c14bcba54cbb4376f7f490
Source dataset
uspto-grants-2016_09
Patent number
US09439888B2

Reaction notes

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