Chloroacetyl chloride → Acetamide, N-(5-hydroxy-1-naphthalenyl)-

HRID 395225

Reaction equation

[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[OH:12].C(=O)([O-])[O-].[Ca+2].Cl[CH2:19][C:20](Cl)=[O:21]>O1CCOCC1>[OH:12][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:8]=1[CH:9]=[CH:10][CH:11]=[C:2]2[NH:1][C:20](=[O:21])[CH3:19]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 5-amino-1-naphthol (17.6 g; 0.11 mol) in 500 ml of dioxane, there were added 11 g of calcium carbonate (0.11 mol) and, dropwise, 8 ml of chloroacetyl chloride (0.112 mol), with stirring and under an inert atmosphere. The reaction medium was heated at 80° C. for 2 hours 30 minutes. The suspension was cooled to room temperature, filtered on sintered glass and the inorganic salts were rinsed twice with dioxane. The mixture of the organic solutions was concentrated until an insoluble product appeared, and then poured over 400 ml of ice-cold water. The precipitate formed was drained, washed once with water and once with pentane. The brown powder obtained was dried under vacuum to a constant weight to give 16.8 g of N-(5-hydroxynaphthalen-1-yl)acetamide with a yield of 76%.

Workup

temperatureThe suspension was cooled to room temperature
filtrationfiltered on sintered glass
washthe inorganic salts were rinsed twice with dioxane
additionThe mixture of the organic solutions
concentrationwas concentrated until an insoluble product
additionpoured over 400 ml of ice-cold water
customThe precipitate formed
washwashed once with water and once with pentane
customThe brown powder obtained
customwas dried under vacuum to a constant weight

Sources & evidence

ORD record: ord-55fcf9a0869941169b9bf0431bf74234
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605124B1

Linked notes

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