3-Chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide → 3-Chloro-6-methoxy-[1,5]naphthyridine-4-carbaldehyde

HRID 2273261Notes

Reaction equation

HRID 2273261 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12](N)=[O:13])=[N:9][C:8]([O:15][CH3:16])=[CH:7][CH:6]=2>O1CCCC1.Cl.C1([Zr]C2C=CC=C2)C=CC=C1>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]=[O:13])=[N:9][C:8]([O:15][CH3:16])=[CH:7][CH:6]=2

Participants

4

Reactant 1

HCID 672571323-Chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide

Product 1

HCID 866715503-Chloro-6-methoxy-[1,5]naphthyridine-4-carbaldehydeYield 39.6%

Reagents, catalysts & solvents 2

HCID 178420596HCID 178420596, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Bis(cyclopentadienyl)zirconium hydrochloride (814 mg, 3.2 mmol, 1.5 eq) is added at room temperature to a stirred solution of 3-chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide (500 mg, 2.1 mmol, 1.0 eq) in tetrahydrofuran (35 mL). After 10 minutes stirring at room temperature, the reaction mixture is filtered through decalite, concentrated and purified by column chromatography (silica gel, eluent: ethyl acetate:petroleum ether, 1:8, v/v) to afford 3-chloro-6-methoxy-[1,5]naphthyridine-4-carbaldehyde as an off-white solid (185 mg, 28% yield).

Workup

  1. filtrationthe reaction mixture is filtered through decalite,
  2. concentrationconcentrated
  3. custompurified by column chromatography (silica gel, eluent: ethyl acetate:petroleum ether, 1:8, v/v)

Sources & evidence

ORD record
ord-0ca58ee815d64982bbabecf010acd922
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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