Hydrochloric Acid → N-(5-Hydroxynaphthalen-1-yl)-2-methylprop-2-enamide

HRID 903980

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:13](Cl)(=[O:17])[C:14]([CH3:16])=[CH2:15].C(=O)([O-])[O-].[Na+].[Na+].Cl>COC1C=CC(O)=CC=1.CO.O.N1C=CC=CC=1>[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:13](=[O:17])[C:14]([CH3:16])=[CH2:15]

Participants

Conditions

Temperature: -10 °C

Procedure

Into a mixture comprising 227 g of 5-amino-α-naphthol, 1 g of hydroquinone monomethyl ether and 2 liters of pyridine was dropwise added with stirring 110 g of methacrylic acid chloride cooled to -10° C. by the use of a coolant. After completion of the addition, the mixture was stirred at 0°-3° C. for 2 hours, followed by stirring at 25° C. for 2 hours. Thereafter, the reaction liquid was poured into 20 liters of water to form a precipitate which was then filtered, water-washed and then dried to obtain solids. The solids were added to 2 liters of a 1:1 mixture of methanol and a 5% sodium carbonate solution, and after stirring at 40° C. the mixture was poured into 4 liters of a 5% hydrochloric acid to form a large amount of precipitate. The precipitate was filtered by suction and then recrystallized from ethanol to obtain 210 g of N-(5-hydroxy-α-naphthyl)methacrylamide, m.p. 223°-224° C.

Workup

additionAfter completion of the addition
stirringby stirring at 25° C. for 2 hours
customThereafter, the reaction liquid
customto form a precipitate which
filtrationwas then filtered
washwater-washed
customdried
customto obtain solids
customto form a large amount of precipitate
filtrationThe precipitate was filtered by suction
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-3d8de8fd46fc46848278ac069620c27c
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04229514

Linked notes

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