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

HRID 533143
Notes
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Reaction equation

HRID 533143 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 699934-Methyloxybenzyl chlorideHCID 23665647Potassium tert-butoxideHCID 722129652-Chloro-7,8-dihydro-1,6-naphthyridin-5(6H)-one

Product 1

HCID 866675022-chloro-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. concentrationconcentrated
  2. custompurified by silica chromatography (0 to 100% EtOAc in Hexanes)
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes