4-Methyloxybenzyl chloride → 2-chloro-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

HRID 533143Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[NH:7][CH2:6][CH2:5][C:4]=2[N:3]=1.CC([O-])(C)C.[K+].[CH3:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[N:7]([CH2:25][C:24]3[CH:27]=[CH:28][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)[CH2:6][CH2:5][C:4]=2[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2-chloro-7,8-dihydro-6H-[1,6]naphthyridin-5-one, (1.6 g, 8.77 mmol) was dissolved in DMF (20 mL) and treated with KOtBu (1.3 g, 10.7 mmol), followed by p-methoxybenzyl chloride (1.6 mL, 11.8 mmol). The mixture was heated to 60° C. for 2 h, concentrated and purified by silica chromatography (0 to 100% EtOAc in Hexanes) to give the compound. LC-MS (M+H)=303.2.

Workup

concentrationconcentrated
custompurified by silica chromatography (0 to 100% EtOAc in Hexanes)
customto give the compound

Sources & evidence

ORD record: ord-37b5b763008645c7b6ab3c0a2d4e38d5
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853237B2

Reaction notes

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