Water → Methyl 5-chloro-2-methyl-3-nitrobenzoate

HRID 2208951Notes

Reaction equation

HRID 2208951 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:15](=O)([O-])[O-].[Na+].[Na+].CI.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:15])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 230097625-Chloro-2-methyl-3-nitrobenzoic acid

Product 1

HCID 53399191Methyl 5-chloro-2-methyl-3-nitrobenzoateYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 5-chloro-2-methyl-3-nitrobenzoic acid (6.75 g, 31.3 mmol) in DMF (33 mL), were added sodium carbonate (13.2 g, 125 mmol) and methyl iodide (17.8 g, 125 mmol). The mixture was heated at 60° C. for 4 h. Water was added to the reaction mixture followed by extraction with dichloromethane. The combined organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography over silica gel to afford the title compound (6.0 g, 84%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-87800a4463f34e4b8e20e526a443f944
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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