Acetic Acid → Methyl 4-amino-3-methyl-5-nitrobenzoate

HRID 18610Notes

Reaction equation

HRID 18610 reaction equation
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:14].[CH3:15][Si](C=[N+]=[N-])(C)C.C(O)(=O)C>C(Cl)Cl.CO.CCCCCC>[CH3:15][O:7][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]([NH2:1])=[C:3]([CH3:14])[CH:4]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 167693Trimethylsilyldiazomethane2×HCID 4590034-Amino-3-methyl-5-nitrobenzoic acid

Product 1

HCID 21098151Methyl 4-amino-3-methyl-5-nitrobenzoate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent2×

Procedure

500 mg (2.50 mmol) 4-Amino-3-methyl-5-nitro-benzoic acid were dissolved in a mixture of 8 mL CH2Cl2 and 2 mL MeOH. At 0° C. 1.3 mL of a 2 M trimethylsilyldiazomethane-solution in hexane were added. After 1 h at 0° C. the reaction mixture was allowed to warm to room temperature. The next day further 1.3 mL of a 2 M trimethylsilyldiazomethane-solution in hexane were added. After stirring for 3 h at room temperature a solution of 0.22 mL acetic acid in 1.8 mL CH2Cl2 was added dropwise to destroy excess trimethylsilyldiazomethane. The reaction mixture was concentrated under reduced pressure. The residue was digerated with heptane and the crystalline material was filtered off to give pure 4-Amino-3-methyl-5-nitro-benzoic acid methyl ester. Yield: 496 mg MS (ES+): m/e=211.

Workup

  1. customAt 0° C
  2. additionwas added dropwise
  3. customto destroy excess trimethylsilyldiazomethane
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. filtrationthe crystalline material was filtered off

Sources & evidence

ORD record
ord-eab67acb25dd49be85c191afc8197a5b
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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