Anthrone → 1-(9-Anthryloxy)-2-aminoethane

HRID 518945Notes

Reaction equation

HRID 518945 reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[K+].O1[CH2:22][CH2:21][NH:20]C1=O>>[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[O:15][CH2:22][CH2:21][NH2:20])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 7018AnthroneHCID 14797Potassium HydroxideHCID 739492-Oxazolidinone

Product 1

HCID 143732341-(9-Anthryloxy)-2-aminoethaneYield 35.2%

Procedure

ExxonMobil™ Aromatic 100 solvent vvas added into a 3-neck round bottom flask containing anthrone (10 g, 51.5 mmol) at room temperature. Potassium hydroxide pellets (0.33 g, 5.15 mmol) and 2-oxazolidinone (7.62 g, 87.5 mmol) were added, and the reaction mixture was heated to reflux and stirred for 2.5 h under nitrogen. The reaction mixture was cooled to room temperature, decanted, and filtered. The solvent was evaporated in vacuo to give 4.3 g (35%) of the desired amine. The crude reaction mixture could be further purified by flash column chromatography. 1H NMR (DMSO-d6, 400 MHz) δ 8.38-8.31 (m, 3H), 8.08-8.02 (m, 2H), 7.56-7.47 (m, 4H), 4.13 (dd, 2H, J=5.58, 5.58 Hz), 3.15 (dd, 2H, J=5.60, 5.60 Hz), 2.91 (bs, 2H). 13C NMR (DMSO-d6, 400 MHz) δ 150.7, 132.8, 128.4, 125.6, 125.4, 124.1, 122.1, 121.9, 78.2, 42.1.

Workup

  1. additionExxonMobil™ Aromatic 100 solvent vvas added into a 3-neck round bottom flask
  2. additionwere added
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux
  5. customdecanted
  6. filtrationfiltered
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fc1cc4334ef141b3a05fee7c4b44a493
Source dataset
uspto-grants-2015_08
Patent number
US09115237B2

Reaction notes

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