7-(4-methoxybenzyl)-4-chloro-3-(chloromethyl)-1,7-naphthyridin-8(7H)-one → HCID 58466449, compound

HRID 1668979Notes

Reaction equation

HRID 1668979 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][N:8]2[C:17](=[O:18])[C:16]3[N:15]=[CH:14][C:13]([CH2:19]Cl)=[C:12]([Cl:21])[C:11]=3[CH:10]=[CH:9]2)=[CH:5][CH:4]=1>[Ni].O.C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:17](=[O:18])[C:16]3[N:15]=[CH:14][C:13]([CH3:19])=[C:12]([Cl:21])[C:11]=3[CH:10]=[CH:9]2)=[CH:22][CH:23]=1

Participants

5

Reactant 1

HCID 584664817-(4-methoxybenzyl)-4-chloro-3-(chloromethyl)-1,7-naphthyridin-8(7H)-one

Product 1

HCID 58466449HCID 58466449, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

Raney Nickel 2800, slurry in H2O, active catalyst (2.5 g, 43 mmol) (wet weight) was rinsed off with ethanol and added to a suspension of 7-(4-methoxybenzyl)-4-chloro-3-(chloromethyl)-1,7-naphthyridin-8(7H)-one (1.00 g, 2.9 mmol) in 50 ml of EtOH. The reaction was stirred at RT for 30 min and then filtered off through a small pad of celite. The filtrate was concentrated under reduced pressure to give 7-(4-methoxybenzyl)-4-chloro-3-methyl-1,7-naphthyridin-8(7H)-one as a clear film. MS (M+H)+ 315.

Workup

  1. filtrationfiltered off through a small pad of celite
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-99cd69e46e9e461295956513433b7d96
Source dataset
uspto-grants-2011_08
Patent number
US07989461B2

Reaction notes

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