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

HRID 2208693Notes

Reaction equation

HRID 2208693 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 a stirred solution of 5-chloro-2-methyl-3-nitrobenzoic acid, prepared analogously to above, (6.75 g, 31.3 mmol) in DMF (33 mL) was added sodium carbonate (13.2 g, 125 mmol) and methyl iodide (17.8 g, 125 mmol). The resulting mixture was heated at 60° C. for 4 h. On completion, water was added to the mixture and extraction was carried out using DCM. Combined organic layers were dried, concentrated under reduced pressure and purified by column chromatography over silica to give methyl 5-chloro-2-methyl-3-nitrobenzoate (6 g, 83.6%).

Workup

  1. customCombined organic layers were dried
  2. concentrationconcentrated under reduced pressure
  3. custompurified by column chromatography over silica

Sources & evidence

ORD record
ord-c9160d22a81b41dfa88b89a076179f76
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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