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

HRID 903980

Reaktionsgleichung

Reaktionsgleichung von HRID 903980
[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]

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 13528Methacryloyl chlorideHCID 657465-Amino-1-naphthol

Produkt 1

HCID 19799964N-(5-Hydroxynaphthalen-1-yl)-2-methylprop-2-enamideAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 90154-MethoxyphenolKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-3d8de8fd46fc46848278ac069620c27c
Quelldatensatz
uspto-grants-1980_10
Patentnummer
US04229514

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