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

HRID 2208792Notes

Reaction equation

HRID 2208792 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 83.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

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 (13.23 g, 125 mmol) and methyl iodide (17.77 g, 125 mmol). The mixture was heated at 60° C. for 4 h. On completion, water was added to the reaction mass and extraction was carried out using DCM. The combined organic layers were dried, concentrated under reduced pressure, and purified by column chromatography over silica gel (to afford the title compound (6.0 g, 83%).

Workup

  1. customThe combined organic layers were dried
  2. concentrationconcentrated under reduced pressure
  3. custompurified by column chromatography over silica gel (

Sources & evidence

ORD record
ord-c4ff4658160b4956a686e8dd68c37860
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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