Water → Methyl 4-methoxy-2-nitrobenzoate

HRID 1892162Notes

Reaction equation

HRID 1892162 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[CH2:15]1CCN2C(=NCCC2)CC1.IC.O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:15])=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2886574-Methoxy-2-nitrobenzoic acid

Product 1

HCID 17733355Methyl 4-methoxy-2-nitrobenzoateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-methoxy-2-nitrobenzoic acid (10.0 g, 50.7 mmol) in DMF (200 mL) at 0° C. was added DBU (15.2 mL, 101 mmol) followed by iodomethane (9.47 mL, 152 mmol). The reaction mixture was allowed to stir at 0° C. for 15 min then at rt overnight. The mixture was poured into water and extracted with EtOAc. The organic solutions were combined, washed with brine and dried over MgSO4. The residue was purified by column chromatography to give methyl 4-methoxy-2-nitrobenzoate (50.7 mmol, 85%) as a yellow solid. LCMS (FA): m/z=212.1 (M+H).

Workup

  1. customat rt
  2. customovernight
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4a33469655464feba4418f0ec4632239
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

Loading…