Sodium Carbonate → 3-(2,6-dichloro-3-nitro-phenyl)-1H-[1,6]naphthyridin-2-one

HRID 270694

Reaction equation

HRID 270694 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[CH2:12][C:13]([NH:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[CH:22]=O)=[O:14].C([O-])([O-])=O.[Na+].[Na+]>CO>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[C:3]=1[C:12]1[C:13](=[O:14])[NH:15][C:16]2[C:17]([CH:22]=1)=[CH:18][N:19]=[CH:20][CH:21]=2

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 598338592-(2,6-dichloro-3-nitro-phenyl)-N-(3-formyl-pyridin-4-yl)-acetamide

Product 1

HCID 598339183-(2,6-dichloro-3-nitro-phenyl)-1H-[1,6]naphthyridin-2-oneYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(2,6-dichloro-3-nitro-phenyl)-N-(3-formyl-pyridin-4-yl)-acetamide (5.0 g, 14.12 mmol) and Na2CO3 (2.5 g) in MeOH (300 mL) is heated for 15 minutes at 70° C. After filtration of the reaction mixture, the solvent is removed by concentration to give crude product, which is purified by flash silica gel column elute with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (93/7%) to give the titled intermediate as a solid (3.75 g, 77.7%).

Workup

  1. filtrationAfter filtration of the reaction mixture
  2. customthe solvent is removed by concentration
  3. customto give crude product, which
  4. customis purified by flash silica gel column
  5. washelute with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (93/7%)

Sources & evidence

ORD record
ord-4b99fbcd4e8446b9be2e524b54b79be4
Source dataset
uspto-grants-2008_11
Patent number
US07449582B2

Linked notes

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