Chlorosuccinimide → 8-chloro-7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one

HRID 577543Notes

Reaction equation

HRID 577543 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][C:12]2=[O:15])=[CH:7][N:6]=1)[CH3:3].C1C(=O)N([Cl:23])C(=O)C1>CC(O)=O>[Cl:23][C:14]1[C:5]([O:4][CH:2]([CH3:1])[CH3:3])=[N:6][CH:7]=[C:8]2[C:13]=1[C:12](=[O:15])[NH:11][CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 867237727-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one

Product 1

HCID 867237738-chloro-7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-oneYield 69.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one (112d, 75 mg, 0.36 mmol)) and NCS (498 mg, 3.64 mmol) in AcOH (3 mL) was heated at 100° C. for 4.5 hours. The reaction mixture was cooled to room temperature, AcOH was removed under vacuum and the residue was purified by column chromatography (0-80% ethyl acetate/heptanes) to give 8-chloro-7-(propan-2-yloxy)-3,4-dihydro-2,6-naphthyridin-1(2H)-one (112e, 60 mg, 68%) as a white solid.

Workup

  1. customAcOH was removed under vacuum
  2. customthe residue was purified by column chromatography (0-80% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-8ad2a543ba3148b4a3fe7a99bcc39024
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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