Hydroquinone → 2-Methyl-N-[(morpholin-4-yl)methyl]prop-2-enamide

HRID 1076442Notes

Reaction equation

HRID 1076442 reaction equation
[CH2:1]([NH:3][C:4](=[O:8])[C:5]([CH3:7])=[CH2:6])O.C1(C=CC(O)=CC=1)O.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>O>[N:17]1([CH2:1][NH:3][C:4](=[O:8])[C:5]([CH3:7])=[CH2:6])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 8083MorpholineHCID 70208Methylolmethacrylamide

Product 1

HCID 215368232-Methyl-N-[(morpholin-4-yl)methyl]prop-2-enamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 300 cc capacity round bottom flask equipped with a stirrer were put 57.5 g (0.5 mole) of N-methylolmethacrylamide and 50 cc of water and, as a polymerization inhibitor, 500 mg of hydroquinone. On the other hand, 43 g (0.5 mole) of morpholine were gradually added thereto while stirring. Afterwards, the contents were stirred for 1 hour at 50°-60°C. Finally, the reaction mixture was concentrated and then was recrystallized from ethyl acetate. m.p.; 78.0°C. Yield: 48.3 g (52.5%).

Workup

  1. customIn a 300 cc capacity round bottom flask equipped with a stirrer
  2. stirringAfterwards, the contents were stirred for 1 hour at 50°-60°C
  3. concentrationFinally, the reaction mixture was concentrated
  4. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-27a9a10f9700442eadc503b7d1c00b7c
Source dataset
uspto-grants-1976_05
Patent number
US03957492

Reaction notes

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