2-Naphthoyl chloride → N-(2-Hydroxyethyl)naphthalene-2-carboxamide

HRID 1942365Notes

Reaction equation

HRID 1942365 reaction equation
CO[CH:3]([O:6]C)[CH2:4][NH2:5].[CH:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[C:18](Cl)=[O:19]>O1CCOCC1>[OH:6][CH2:3][CH2:4][NH:5][C:18]([C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=1)=[O:19]

Participants

4

Reactant 2

HCID 752462-Naphthoyl chlorideHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 13288324N-(2-Hydroxyethyl)naphthalene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 3.15 g (30 mmol) 2,2-dimethoxy-ethylamine and 40 mL dioxane is added 1.91 g (10 mmol) naphthalene-2-carbonyl chloride. After stirring overnight the solution is pored into 200 mL of ice water. Filtration yields the product in almost quantitative yield as a white solid.

Workup

  1. filtrationFiltration
  2. customyields the product in almost quantitative yield as a white solid

Sources & evidence

ORD record
ord-22dc84693c8b474c9b551faa67a61a3e
Source dataset
uspto-grants-2013_03
Patent number
US08389555B2

Reaction notes

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