Ethanolamine → N-(2-hydroxyethyl)-4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetamide

HRID 2225757Notes

Reaction equation

HRID 2225757 reaction equation
CO[C:3](=[O:26])[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:7][CH:6]=1.[CH2:27]([CH2:29][NH2:30])[OH:28]>CO.O1CCCC1>[OH:28][CH2:27][CH2:29][NH:30][C:3](=[O:26])[C:4](=[O:25])[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 700EthanolamineHCID 541704664-[2-(2-Naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl ester

Product 1

HCID 19004283N-(2-hydroxyethyl)-4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetamideYield 53.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.5 g) in methanol (40 mL) and tetrahydrofuran (10 mL) was treated with ethanolamine (0.094 g) and the mixture was refluxed for 48 hours. The solvents were removed by evaporation and the residue was purified by HPLC (ethyl acetate-methanoltriethylamine; 95:5:2) followed by crystallization from tetrahydrofuran-ethyl alcohol to give 0.29 g of N-(2-hydroxyethyl)-4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetamide as a colorless solid, mp 138°-140° C.

Workup

  1. temperaturethe mixture was refluxed for 48 hours
  2. customThe solvents were removed by evaporation
  3. customthe residue was purified by HPLC (ethyl acetate-methanoltriethylamine; 95:5:2)
  4. customfollowed by crystallization from tetrahydrofuran-ethyl alcohol

Sources & evidence

ORD record
ord-ad2fbfc2f79847989c09f1c4b474745d
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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