Ethanolamine → 7-Hydroxycoumarin-3-(N-(2-hydroxyethyl))carboxamide

HRID 1680383Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][OH:4].[OH:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[C:11]([C:17](Cl)=[O:18])[C:12](=[O:16])[O:13]2)=[CH:8][CH:7]=1>O1CCOCC1>[OH:4][CH2:3][CH2:2][NH:1][C:17]([C:11]1[C:12](=[O:16])[O:13][C:14]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[C:6]([OH:5])[CH:15]=2)=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold, stirred solution of 3.05 grams (g) [0.05 mole (mol)] of 2-aminoethanol in 30 milliliters (ml) of dioxane was added a suspension of 2.2 g (0.01 mol) of 7-hydroxycoumarin-3-carbonyl chloride [Sherman et al, Anal. Chem. 40:803(1968)] in 75 ml of dioxane. The mixture was stirred at 0° C. for 30 minutes, during which time a thick oil precipitated that solidified upon scratching with a spatula. The dioxane was decanted and the precipitate dissolved in water. Adjustment of the pH of the aqueous solution to 7.0 with glacial acetic acid resulted in precipitation of a tan solid. The solid precipitate was recrystallized from water to give 1.3 g (52% yield) of N-(2-hydroxyethyl)-7-hydroxycoumarin-3-carboxamide as a white solid with a melting point of 244°-245° C. Elemental analysis and infrared spectral data for the product are given below:

Workup

additionwas added
customprecipitated that solidified
customThe dioxane was decanted
dissolutionthe precipitate dissolved in water
customAdjustment of the pH of the aqueous solution to 7.0 with glacial acetic acid resulted in precipitation of a tan solid
customThe solid precipitate was recrystallized from water

Sources & evidence

ORD record: ord-7bba79ae782b4c10a1eddabef093c86c
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04273715

Reaction notes

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