3,5-Dinitroaniline → 1,3,5-Triaminobenzene

HRID 2419606Notes

Reaction equation

HRID 2419606 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[C:9]([N+:11]([O-])=O)[CH:10]=1)[NH2:7])([O-])=O>[Pd].C(OCC)(=O)C>[C:6]1([NH2:7])[CH:5]=[C:4]([NH2:1])[CH:10]=[C:9]([NH2:11])[CH:8]=1

Participants

4

Reactant 1

HCID 120683,5-Dinitroaniline

Product 1

HCID 669521,3,5-TriaminobenzeneYield 66.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 10.0 g of 3,5-dinitroaniline, 1.0 g of 10% palladium on carbon catalyst and 100 ml of ethyl acetate is hydrogenated in a Parr shaker for 1 hour at room temperature. The mixture is warmed and decanted. The insoluble material in the flask is dissolved in 100 ml of hot acetonitrile and is filtered through diatomaceous earth. The filtrate is evaporated to a small volume and is crystallized from ethyl acetate to give 4.45 g of 1,3,5-benzenetriamine as a tan powder.

Workup

  1. temperatureThe mixture is warmed
  2. customdecanted
  3. dissolutionThe insoluble material in the flask is dissolved in 100 ml of hot acetonitrile
  4. filtrationis filtered through diatomaceous earth
  5. customThe filtrate is evaporated to a small volume
  6. customis crystallized from ethyl acetate

Sources & evidence

ORD record
ord-c591bf6fce1d4ccdb8463a71641d9b9a
Source dataset
uspto-grants-1978_08
Patent number
US04107201

Reaction notes

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