2-Naphthol → 2-(2-Aminoethoxy)naphthalene

HRID 576022Notes

Reaction equation

HRID 576022 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[OH-].[K+].O1[CH2:18][CH2:17][NH:16]C1=O.C(O)C(O)C(O)C(O)C(O)C=O.[O-]S([O-])(=O)=O.[Mg+2]>C(N)CN>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:18][CH2:17][NH2:16]

Participants

6

Reactant 4

HCID 86632-Naphthol2×HCID 14797Potassium HydroxideHCID 739492-Oxazolidinone2×HCID 21924827Magnesium;2,3,4,5,6-pentahydroxyhexanal;sulfate

Product 1

HCID 27942452-(2-Aminoethoxy)naphthaleneYield 97.6%

Reagents, catalysts & solvents 1

HCID 3301EthylenediamineCatalyst

Conditions

Temperature
70 °C

Procedure

2-naphthol (200 g, 1.39 mol) at room temperature. Potassium hydroxide pellets (8.99 g, 0.139 mol) and 2-oxazolidinone (181 g, 2.08 mol) were then added, and the reaction mixture was heated to reflux and stirred for 5.5 h. Reaction was monitored by TLC analysis. Additional 2-oxazolidinone (24.0 g, 0.277 mol) was added to ensure complete conversion of the 2-naphthol and the reaction mixture was heated to reflux temperature for 16 additional hours. The reaction mixture was cooled to 70° C. and ethylenediamine (18.5 mL, 0.277 mmole) was added. The reaction mixture was then reheated to reflux temperature (approximately 155° C.) under nitrogen and stirred for approximately 6 hours. The reaction mixture was cooled to room temperature and Magnesol® was added and stirred into the reaction mixture for 15 minutes. The reaction mixture was then filtered over Celite® and reaction flask was washed three times with ExxonMobil™ Aromatic 100 solvent. The filtrate was collected and the solvent was evaporated in vacuo to obtain 254.1 g (97%) of 2-(2-naphthoxy)ethylamine. Purity was determined by HPLC and NMR analysis to be ˜92%.

Workup

  1. customat room temperature
  2. additionwere then added
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux
  5. customReaction
  6. temperaturethe reaction mixture was heated
  7. temperatureto reflux temperature for 16 additional hours
  8. temperatureto reflux temperature (approximately 155° C.) under nitrogen
  9. stirringstirred for approximately 6 hours
  10. temperatureThe reaction mixture was cooled to room temperature
  11. stirringstirred into the reaction mixture for 15 minutes
  12. filtrationThe reaction mixture was then filtered over Celite® and reaction flask
  13. washwas washed three times with ExxonMobil™ Aromatic 100 solvent
  14. customThe filtrate was collected
  15. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-aecfb4fbc93d4aa9a149e93d73da72f3
Source dataset
uspto-grants-2015_05
Patent number
US09035097B2

Reaction notes

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