Ethylenediamine → Anthracene

HRID 1470061Notes

Reaction equation

HRID 1470061 reaction equation
N[CH2:2][CH2:3]N.[C:5]([CH2:8][C:9](=O)[CH3:10])(=O)[CH3:6]>C(O)C>[CH:3]1[CH:2]=[C:10]2[C:8]([CH:9]=[C:10]3[C:8](=[CH:9]2)[CH:5]=[CH:6][CH:3]=[CH:2]3)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 31261Acetylacetone

Product 1

HCID 8418AnthraceneYield 129.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Prepared by the method of McCarthy, P. J., et al., J. Am. Chem. Soc., 1955, 77, 5820. 1,2-Diaminoethane (1) (3.0 g, 3.3 mL, 49.9 mmol) was dissolved in ethanol (70 mL) and acetylacetone (2) (10.3 mL, 99.8 mmol) was added in a steady stream over a period of about 10 minutes whilst stirring the reaction mixture. The reaction was refluxed for 3 hours. After cooling, evaporation of the solvent in vacuo left a yellow solid which was purified by the addition of diethyl ether (ca. 100 mL). The desired ligand (3) (7.3 g, 32.4 mmol, 65%) was obtained as an off-white crystalline solid by suction filtration.

Workup

  1. customPrepared by the method of McCarthy, P
  2. temperatureThe reaction was refluxed for 3 hours
  3. temperatureAfter cooling
  4. customevaporation of the solvent in vacuo
  5. waitleft a yellow solid which
  6. customwas purified by the addition of diethyl ether (ca. 100 mL)

Sources & evidence

ORD record
ord-3d208d1a96ae4c049013a1206ed7475d
Source dataset
uspto-grants-2015_04
Patent number
US09006425B2

Reaction notes

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