Allylamine → 1-Allyl 3-diphenylmethoxy-6-hydroxymethyl-4-pyridone

HRID 704655Notes

Reaction equation

HRID 704655 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[CH:7][CH:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14](OC)=[CH:13][CH:12]=2)[C:5](=[O:19])[CH:4]=1.[CH2:20](N)[CH:21]=[CH2:22].C(O[CH2:28][CH3:29])(=O)C>CO>[CH2:20]([N:8]1[C:3]([CH2:2][OH:1])=[CH:4][C:5](=[O:19])[C:6]([O:9][CH:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:29]2[CH:28]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:7]1)[CH:21]=[CH2:22]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 8857Ethyl AcetateHCID 200727056-Hydroxymethyl-3-(p-methoxybenzyl)oxy-4-pyridone

Product 1

HCID 150581941-Allyl 3-diphenylmethoxy-6-hydroxymethyl-4-pyridone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1.542 g of 6-hydroxymethyl-3-(p- methoxybenzyl)oxy-4-pyridone in methanol is 5.710 g of allylamine at room temperature, and the mixture is stirred for 14 hours. After condensing at reduced pressure, 20 ml of ethyl acetate is added to the residue to perform crystallization. After the mixture is left standing at 4° C. for 4 hours, the crystal is collected by filtration, washed with a small amount of ethyl acetate and dried under reduced pressure to give 1.050 g of the title compound.

Workup

  1. customat room temperature
  2. additionis added to the residue
  3. customcrystallization
  4. waitAfter the mixture is left
  5. waitstanding at 4° C. for 4 hours
  6. filtrationthe crystal is collected by filtration
  7. washwashed with a small amount of ethyl acetate
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-9dbc1f7c7e8b4721b4fcb90dbff196ec
Source dataset
uspto-grants-1991_01
Patent number
US04988686

Reaction notes

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