Dimethyl Sulfate → Methyl 4-(methylamino)-3-nitrobenzoate

HRID 1393685Notes

Reaction equation

HRID 1393685 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[OH-].[Na+].[C:17](=O)([O-])[O-].[K+].[K+].COS(=O)(=O)OC>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:17][NH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 3941008Methyl 4-amino-3-nitrobenzoate

Product 1

HCID 7650848Methyl 4-(methylamino)-3-nitrobenzoateYield 98%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

Methyl 4-amino-3-nitrobenzoate (7.0 g), sodium hydroxide (5.7 g), potassium carbonate (4.9 g) and tetrabutylammonium bromide (0.22 g) were suspended in toluene (100 ml). The mixture was stirred for 1 hour at 40° C., and then dimethylsulfuric acid (7.7 ml) was added thereto and stirred for 2 hours. The reaction solution was extracted with ethyl acetate, and the extract was washed with water and dried over sodium sulfate anhydrous. The product was concentrated under reduced pressure to give methyl 4-methylamino-3-nitrobenzoate (7.3 g, Y.:97%).

Workup

  1. stirringstirred for 2 hours
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialdried over sodium sulfate anhydrous
  5. concentrationThe product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f2f4374795174b6f910bd8bfe8ac31fd
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

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