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

HRID 2208684Notes

Reaction equation

HRID 2208684 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.C(Cl)Cl>[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

7

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 83.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To stirred solution of 5-chloro-2-methyl-3-nitrobenzoic acid (6.75 g, 31.25 mmol) in DMF (33 mL), sodium carbonate (13.23 g, 125.18 mmol) and methyl iodide (17.77 g, 125.2 mmol) were added. Resulting reaction mass was heated at 60° C. for 4 h. On completion, water was added to the reaction mass and extraction was carried out using DCM. Combined organic layers were dried, concentrated under reduced pressure and purified by column chromatography over silica (60-120 mesh size) giving desired compound (6 g, 83%).

Workup

  1. additionwere added
  2. customResulting
  3. customreaction mass
  4. customCombined organic layers were dried
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography over silica (60-120 mesh size)

Sources & evidence

ORD record
ord-8b10aafe1752468388bcc337d5001453
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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