Hydroxyamine hydrochloride → 5-p-Methoxybenzyloxy-1-hydroxy-2-hydroxymethyl-4-pyridone

HRID 1086179Notes

Reaction equation

HRID 1086179 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C:9]2[C:10](=[O:17])[CH:11]=[C:12]([CH2:15][OH:16])O[CH:14]=2)=[CH:5][CH:4]=1.Cl.[NH2:21][OH:22]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][O:8][C:9]2[C:10](=[O:17])[CH:11]=[C:12]([CH2:15][OH:16])[N:21]([OH:22])[CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 104916984H-Pyran-4-one, 2-(hydroxymethyl)-5-[(4-methoxyphenyl)methoxy]-

Product 1

HCID 107076455-p-Methoxybenzyloxy-1-hydroxy-2-hydroxymethyl-4-pyridone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

39.3 g of 5-p-methoxybenzyloxy-2-hydroxymethyl-4-pyrone is dissolved in 600 ml of pyridine, then 52.2 g of hydroxylamine hydrochloride is added thereto, and reacted at 70°-75° C. for 2.5 hours. After the reaction, the reaction mixture is concentrated to about 100 ml and, after adding 100 ml of water thereto, added to a mixed solution of 75 ml of hydrochloric acid and 225 ml of water with ice cooling. The pH is adjusted to 2-2.5, and stirring is conducted at the same temperature for 30 minutes. The formed crystals are filtered off, washed with water and then dried to obtain 16.6 f of the title compound.

Workup

  1. customreacted at 70°-75° C. for 2.5 hours
  2. customAfter the reaction
  3. concentrationthe reaction mixture is concentrated to about 100 ml
  4. additionafter adding 100 ml of water
  5. additionadded to a mixed solution of 75 ml of hydrochloric acid and 225 ml of water with ice cooling
  6. filtrationThe formed crystals are filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-f5208b1528f84175a7e947960fac2e2b
Source dataset
uspto-grants-1991_07
Patent number
US05028601

Reaction notes

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