Methyl Methanesulfonate → Methyl 2-methoxy-4-(N-methylacetamido)-5-nitrobenzoate

HRID 1410219Notes

Reaction equation

HRID 1410219 reaction equation
[C:1]([NH:4][C:5]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:18][CH3:19])[CH:6]=1)(=[O:3])[CH3:2].[CH3:20]S(OC)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[CH3:19][O:18][C:7]1[CH:6]=[C:5]([N:4]([CH3:20])[C:1](=[O:3])[CH3:2])[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 3

HCID 4156Methyl MethanesulfonateHCID 11430Potassium CarbonateHCID 77723Methyl 4-acetamido-2-methoxy-5-nitrobenzoate

Product 1

HCID 10379023Methyl 2-methoxy-4-(N-methylacetamido)-5-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of methyl 4-acetamido-2-methoxy-5-nitrobenzoate (2.0 g; 7.5 mmol), methyl methanesulfonate (0.85 g; 7.7 mmol) and K2CO3 (2.0 g; 14.5 mmol) in DMF (20 mL) was stirred for 36 h at rt. The mixture was thereafter poured into brine and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated to give the crude sub-title compound.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c9f1611cfbcb4514a60a69fa7991acbf
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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