Ethanolamine → 6-(2-Hydroxyethyl-aminocarbonyl)-2-naphthoic acid

HRID 2287946Notes

Reaction equation

HRID 2287946 reaction equation
CO[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:15]([OH:17])=[O:16])[CH:11]=2)[CH:6]=1)=[O:4].[CH2:18]([CH2:20][NH2:21])[OH:19]>>[OH:19][CH2:18][CH2:20][NH:21][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([OH:17])=[O:16])[CH:9]=[CH:8]2)=[O:4]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 33802176-(Methoxycarbonyl)naphthalene-2-carboxylic acid

Product 1

HCID 187029066-(2-Hydroxyethyl-aminocarbonyl)-2-naphthoic acid

Procedure

2.1 g of naphthalene-2,6-dicarboxylic acid monomethyl ester and 25 ml of ethanolamine are heated at 150° C. for 3 h. The excess ethanolamine is distilled off in vacuo, and the residue is dissolved in water and the mixture is extracted with ethyl acetate. After acidifying the aqueous phase, the product which is deposited is filtered off with suction and recrystallized from ethanol. 1.2 g of 6-(2-hydroxyethyl-aminocarbonyl)-2-naphthoic acid are obtained.

Workup

  1. distillationThe excess ethanolamine is distilled off in vacuo
  2. dissolutionthe residue is dissolved in water
  3. extractionthe mixture is extracted with ethyl acetate
  4. filtrationthe product which is deposited is filtered off with suction
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-7f7238c97ffa4653a3967569cb05ce1a
Source dataset
uspto-grants-2000_07
Patent number
US06087304

Reaction notes

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