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

HRID 1406460Notes

Reaction equation

HRID 1406460 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([NH:13][C:14](=[O:16])[CH3:15])=[CH:6][C:5]=1[O:17][CH3:18].[CH3:20]OS(C)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.ClCCl>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([N:13]([C:14](=[O:16])[CH3:15])[CH3:20])=[CH:6][C:5]=1[O:17][CH3:18]

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 6344DichloromethaneSolvent

Procedure

A mixture of 4-acetylamino-2-methoxy-5-nitro-benzoic acid methyl ester (4.0 g, 14.9 mmol), methanesulfonic acid methyl ester (1.3 mL, 15.4 mmol) and K2CO3 (4.0 g, 28.9 mmol) in 40 mL DMF was stirred overnight at ambient temperature. The mixture was poured onto ice water and diluted with dichloromethane. The organic phase was separated, dried and concentrated i.vac.

Workup

  1. additionThe mixture was poured onto ice water
  2. customThe organic phase was separated
  3. customdried
  4. concentrationconcentrated i.vac

Sources & evidence

ORD record
ord-ac114fa1c26e41eab30bb48ba4469019
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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