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

HRID 627291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627291
[OH:1][CH2:2][C:3]1O[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=1.Cl.[NH2:21][OH:22]>N1C=CC=CC=1>[OH:22][N:21]1[CH:5]=[C:6]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:7](=[O:9])[CH:8]=[C:3]1[CH2:2][OH:1]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 107076455-p-Methoxybenzyloxy-1-hydroxy-2-hydroxymethyl-4-pyridoneAusbeute 38,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a stirred solution of 2-(hydroxymethyl)-5-[(4-methoxybenzyl)oxy]-4H-pyran-4-one (Intermediate 289, 101.7 g, 0.388 mol) in pyridine (1.35 L) was added hydroxylamine hydrochloride (134.7 g, 1.94 mol). The reaction mixture was heated at 85° C. for 4 hours, then evaporated to dryness and triturated with water (700 mL). The precipitate was collected by filtration and washed with water (250 mL). The solids were then stirred in isopropanol (100 mL) for 12 hours, collected by filtration and dried under vacuum to afford the title compound as a white solid (41.2 g, 38%).

Aufarbeitung

  1. customevaporated to dryness
  2. customtriturated with water (700 mL)
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water (250 mL)
  5. filtrationcollected by filtration
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fdbc379c943a4301bea49dcc4d69b882
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309245B2

Notizen zur Reaktion

Wird geladen…