Chloride → 6-Chloro-3-phenyl-1,5-naphthyridin-2(1H)-one

HRID 42371Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=O)[C:5]([NH:10][C:11](=[O:17])OC(C)(C)C)=[CH:4][CH:3]=1.[Cl-].[CH2:19]1[CH2:29][CH2:28]N2[C:22](=NCCC2)[CH2:21][CH2:20]1.[CH2:30]1COCC1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:10][C:11](=[O:17])[C:30]([C:22]1[CH:21]=[CH:20][CH:19]=[CH:29][CH:28]=1)=[CH:8]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of tert-butyl (6-chloro-2-formylpyridin-3-yl)carbamate (1-4) (5 g, 19.5 mmol), phenylacethyl chloride (3.3 g, 21.4 mmol), and DBU (9.8 g, 39 mmol) in THF (215 mL) was stirred at room temperature for 2 days and at 100° C. for overnight. The mixture was diluted with CHCl3, washed with water and brine, dried (MgSO4), filtered, and the solvent was removed under reduced pressure. To the residue was added CHCl3, and the resulting solid was collected by filtration to give 6-chloro-3-phenyl-1,5-naphthyridin-2(1H)-one (7-1) as colorless solid.

Workup

washwashed with water and brine
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvent was removed under reduced pressure
additionTo the residue was added CHCl3
filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record: ord-9e8b644fdd414a4ab4ff50a1954391a0
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536193B2

Reaction notes

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