Benzoic acid, 2-methoxy-5-nitro-, methyl ester → HCID 25239184, compound

HRID 1916353Notes

Reaction equation

HRID 1916353 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:4]=1[C:5](OC)=[O:6].[CH3:16][NH2:17].CCO>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:4]=1[C:5]([NH:17][CH3:16])=[O:6]

Participants

4

Reactant 2

HCID 7020925Benzoic acid, 2-methoxy-5-nitro-, methyl esterHCID 22028356Methylamine ethanol

Product 1

HCID 25239184HCID 25239184, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 2-methoxy-5-nitrobenzoate (389 mg, 1.84 mmol) in THF (3.0 mL) was added 33% MeNH2/EtOH solution (2.0 mL, 16.0 mmol) and the mixture was stirred at 20° C. overnight. The solution was evaporated and the residue was chromatographed (SiO2 230-400 mesh) eluting with 7:3 hexanes/EtOAc to remove 2-(methylamino)-5-nitrobenzoate derivatives. Further elution with EtOAc provided the title compound (268.5 mg, 70% yield) as a yellowish solid: LCMS (ES) m/z 211 (M+H).

Workup

  1. customThe solution was evaporated
  2. customthe residue was chromatographed (SiO2 230-400 mesh)
  3. washeluting with 7:3 hexanes/EtOAc
  4. customto remove 2-(methylamino)-5-nitrobenzoate derivatives
  5. washFurther elution with EtOAc

Sources & evidence

ORD record
ord-323e8e9241fc4dd89a13701ce9011c4d
Source dataset
uspto-grants-2013_12
Patent number
US08618115B2

Reaction notes

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