Ethyl Acetate → 4-(2H-1,2,3,4-tetrazol-2-yl)aniline

HRID 1798822Notes

Reaction equation

HRID 1798822 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[N:14]=[N:13][CH:12]=[N:11]2)=[CH:6][CH:5]=1)([O-])=O.C(OCC)(=O)C>C(O)C.[Pd]>[N:11]1[N:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[N:14]=[N:13][CH:12]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 5338832-(4-Nitrophenyl)-2H-tetrazole

Product 1

HCID 5716394-(2H-1,2,3,4-tetrazol-2-yl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(4-Nitrophenyl)-2H-tetrazole (200 mg, 1.05 mmol) was suspended in ethanol (1 mL). Ethyl acetate (1 mL) was added to improved solubility. The solution was degassed and purged with nitrogen 3 times before palladium on carbon (10% w/w, 223 mg, 0.2 mmol) was added. The mixture was degassed and purged with hydrogen 3 times and stirred under a hydrogen balloon for 2 hours. The reaction was diluted with acetone and passed through a plug of silica gel, which was washed thoroughly with acetone. The filtrated was concentrated to give the crude product which was used as isolated.

Workup

  1. customThe solution was degassed
  2. additionwas added
  3. customThe mixture was degassed
  4. custompurged with hydrogen 3 times
  5. additionThe reaction was diluted with acetone
  6. washwas washed thoroughly with acetone
  7. concentrationThe filtrated was concentrated

Sources & evidence

ORD record
ord-bd431c95bcb042a0809cfc1f3f247942
Source dataset
uspto-grants-2013_01
Patent number
US08343990B2

Reaction notes

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