HCID 54706820, compound → 1-(1,2-Dihydro-4-hydroxy-1-phenyl-2-oxo-1,8-naphthyridin-3-yl)-4-hydroxy-piperidinium hydroxide

HRID 1199716Notes

Reaction equation

Br[C:2]1[C:3](=[O:19])[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]2[C:10]([C:11]=1[OH:12])=[CH:9][CH:8]=[CH:7][N:6]=2>N1C(C)=CC=CC=1C.OC1CCNCC1>[OH-:12].[OH:12][C:11]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3](=[O:19])[C:2]=1[NH+:4]1[CH2:5][CH2:10][CH:11]([OH:12])[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 3-bromo-4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one (1 g) in a mixture of 2,6-lutidine (5 mL) and 4-hydroxy-piperidine (3.12 g) was heated at 100° C. for 32 hours. The lutidine was removed by evaporation under high vacuum. The residue was dissolved in CH2CN(20): H2O(80): CH3CO2H(1) and separated by reversed phase preparative HPLC (Whatman Magnum 40 with Partisil 40/ODS-3). The fractions containing the desired product were combined and evaporated to yield a partially crystalline material which was recrystallized from isopropanol to yield the desired product, m.p. 256°-258° C.

Workup

customThe lutidine was removed by evaporation under high vacuum
dissolutionThe residue was dissolved in CH2CN(20)
customH2O(80): CH3CO2H(1) and separated by reversed phase preparative HPLC (Whatman Magnum 40 with Partisil 40/ODS-3)
additionThe fractions containing the desired product
customevaporated
customto yield a partially crystalline material which
customwas recrystallized from isopropanol

Sources & evidence

ORD record: ord-b6be4a5dfd7b4de5803c9bfc9e3e8729
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04902693

Reaction notes

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