Ethanolamine → HCID 86737404, compound

HRID 894374Notes

Reaction equation

HRID 894374 reaction equation
[C:1]12[C:14](=[O:15])[O:13][C:11](=O)[C:2]=1[CH2:3][CH2:4][C:5]1[C:10]2=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:16]([CH2:18][NH2:19])[OH:17]>C(O)(=O)C>[OH:17][CH2:16][CH2:18][N:19]1[C:11](=[O:13])[C:2]2[CH2:3][CH2:4][C:5]3[C:10]([C:1]=2[C:14]1=[O:15])=[CH:9][CH:8]=[CH:7][CH:6]=3

Participants

4

Reactant 2

HCID 700EthanolamineHCID 1422143,4-Dihydro-1,2-naphthalenedicarboxylic anhydride

Product 1

HCID 86737404HCID 86737404, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 70 g (0.35 mol) of 3,4-dihydronaphthalene-1,2-dicarboxylic acid anhydride [prepared according to Org. Synthesis, Col., Vol. 2, 194 (1943)] and 23.5 g (0.385 mol) of ethanolamine in 1.7 liters of glacial acetic acid is kept under reflux for 24 hours. The glacial acetic acid is then removed by distillation, the residue is dissolved in 2 liters of absolute ethanol, 50 g of an ion exchanger ("Dowex 50 W" from Fluka AG) are added and the suspension is kept under reflux for 24 hours. The ion exchanger is then filtered off, the ethanol is distilled off and the residue is recrystallised from diethyl ether/ethanol. This yields 61.8 g (73% of theory) of N-(2'-hydroxyethyl)-3,4-dihydronaphthalene-1,2-dicarboximide; melting point 120.5°-121° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe glacial acetic acid is then removed by distillation
  3. dissolutionthe residue is dissolved in 2 liters of absolute ethanol
  4. addition50 g of an ion exchanger ("Dowex 50 W" from Fluka AG) are added
  5. temperatureunder reflux for 24 hours
  6. filtrationThe ion exchanger is then filtered off
  7. distillationthe ethanol is distilled off
  8. customthe residue is recrystallised from diethyl ether/ethanol

Sources & evidence

ORD record
ord-b7ca3f8b71d3451ab38af7fad0536e64
Source dataset
uspto-grants-1981_08
Patent number
US04283509

Reaction notes

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