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

HRID 578067
Notes
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Reaction equation

HRID 578067 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228DimethylformamideSolvent
HCID 6344
Dichloromethane
Solvent

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

Sources & evidence

ORD record
ord-0979d2351ae0478eb4ffa345f4f7b51a
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040565B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes