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

HRID 627291Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 85 °C

Procedure

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%).

Workup

customevaporated to dryness
customtriturated with water (700 mL)
filtrationThe precipitate was collected by filtration
washwashed with water (250 mL)
filtrationcollected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-fdbc379c943a4301bea49dcc4d69b882
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309245B2

Reaction notes

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