Ethanolamine → HCID 86737404, compound

HRID 355014Notes

Reaction equation

HRID 355014 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. Syntheses, 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-b067f255d8aa443abf7b912c560a7d69
Source dataset
uspto-grants-1983_03
Patent number
US04377669

Reaction notes

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