Ethyl Acetate → HCID 69292323, compound

HRID 270702Notes

Reaction equation

HRID 270702 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[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+].C(OCC)(=O)C>CO>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 86044460HCID 86044460, compound

Product 1

HCID 69292323HCID 69292323, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2,6-Dichloro-4-nitro-phenyl)-N-(3-formyl-pyridin-4-yl)-acetamide (3.0 g, 8.47 mmol) is dissolved in dry methanol (240 mL). Na2CO3 (1.80 g, 16.94 mmol) is added. The reaction is refluxed for 30 minutes, diluted by ethyl acetate (210 mL) and filtered. The solvents are evaporated to give crude product, which is recrystallized by ethyl acetate/hexanes to give 3-(2,6-dichloro-4-nitro-phenyl)-1H-[1,6]-naphthyridin-2-one as a slightly yellow solid (3.07 g).

Workup

  1. temperatureThe reaction is refluxed for 30 minutes
  2. filtrationfiltered
  3. customThe solvents are evaporated
  4. customto give crude product, which
  5. customis recrystallized by ethyl acetate/hexanes

Sources & evidence

ORD record
ord-72ebd631972a49c59b32f90afdb481a6
Source dataset
uspto-grants-2008_11
Patent number
US07449582B2

Reaction notes

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