Methacryloyl chloride → N-(5-Hydroxynaphthalen-1-yl)-2-methylprop-2-enamide

HRID 1646835Notes

Reaction equation

HRID 1646835 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]>COC1C=CC(O)=CC=1.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

5

Reactant 2

HCID 13528Methacryloyl chlorideHCID 657465-Amino-1-naphthol

Product 1

HCID 19799964N-(5-Hydroxynaphthalen-1-yl)-2-methylprop-2-enamideYield 87.8%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 1049PyridineSolvent

Conditions

Temperature
-10 °C

Procedure

227 g of 5-amino-α-naphthol, 1 g of hydroquinone monomethyl ether and 2 litres of pyridine were mixed and cooled to -10° C. by using a freezing medium, and then 110 g of methacrylic acid chloride was added dropwise to the mixture with stirring. After said dropwise addition ended, the solution was stirred at 0°-3° C. for 2 hours, followed by additional 2-hour stirring at 25° C. The reaction solution was poured into 20 litres of ice water. The resultantly formed precipitate was filtered, washed with water and dried. The resulting solids were added into 2 litres of a methanol aqueous 5% sodium carbonate (1/1) mixed solvent, and stirred at 40° C. for 30 minutes and the solution was poured into 4 litres of 5% hydrochloric acid. A large amount of precipitate was formed. This precipitate was suction filtered and recrystallized from ethanol to give 210 g of N-(5-hydroxy-α-naphthyl)methacrylamide having a melting point of 223°-224° C.

Workup

  1. additionaddition
  2. stirringthe solution was stirred at 0°-3° C. for 2 hours
  3. waitfollowed by additional 2-hour
  4. stirringstirring at 25° C
  5. filtrationThe resultantly formed precipitate was filtered
  6. washwashed with water
  7. customdried
  8. additionThe resulting solids were added into 2 litres of a methanol aqueous 5% sodium carbonate (1/1)
  9. additionmixed solvent
  10. stirringstirred at 40° C. for 30 minutes
  11. additionthe solution was poured into 4 litres of 5% hydrochloric acid
  12. customA large amount of precipitate was formed
  13. filtrationfiltered
  14. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6a8cd8da025a4a6aa9bed7c20dcb4699
Source dataset
uspto-grants-1993_01
Patent number
US05182183

Reaction notes

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