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

HRID 270699Notes

Reaction equation

HRID 270699 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][CH: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][CH:19]=[CH:20][CH:21]=2

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 598338822-(2,6-dichloro-3-nitro-phenyl)-N-(2-formyl-phenyl)-acetamide

Product 1

HCID 598339333-(2,6-dichloro-3-nitro-phenyl)-1H-quinolin-2-oneYield 43.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(2,6-dichloro-3-nitro-phenyl)-N-(2-formyl-phenyl)-acetamide (0.7 g, 1.99 mmol) and Na2CO3 (1.0 g) in MeOH (150 mL) is heated for 30 minutes at 70° C. After filtration of the reaction mixture, the solvent is removed by concentration to give crude product. The crude product is purified by flash silica gel column, eluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (97/3%), resulting in the titled intermediate as a solid (0.288 g, 41.3%).

Workup

  1. filtrationAfter filtration of the reaction mixture
  2. customthe solvent is removed by concentration
  3. customto give crude product
  4. customThe crude product is purified by flash silica gel column
  5. washeluting with CH2Cl2 (100%) gradient to CH2Cl2/MeOH (2N NH3) (97/3%)

Sources & evidence

ORD record
ord-3d3e0748fb0640fa9fabbadd280c587a
Source dataset
uspto-grants-2008_11
Patent number
US07449582B2

Reaction notes

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