Methylamine → Benzoic acid, 2-(methylamino)-3-nitro-, methyl ester

HRID 1773741

Reaction equation

HRID 1773741 reaction equation
F[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH3:21][NH2:22]>C(Cl)Cl.O>[CH3:21][NH:22][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 13470961Methyl 2-fluoro-3-nitrobenzoate

Product 1

HCID 59635415Benzoic acid, 2-(methylamino)-3-nitro-, methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 2-fluoro-3-nitrobenzoate (25 g, 0.126 mol) was dissolved in DCM (400 ml) and to this was added Potassium carbonate (34.7 g, 0.25 mol) followed by Methylamine (20.63 ml, 0.5 mol). Reaction was stirred at room temperature under argon. Upon completion reaction was diluted with water and extracted with DCM (3×) then dried over magnesium sulfate. Solvents were removed under reduced pressure to afford methyl 2-(methylamino)-3-nitrobenzoate as a yellow solid.

Workup

  1. customReaction
  2. customUpon completion reaction
  3. extractionextracted with DCM (3×)
  4. dry with materialthen dried over magnesium sulfate
  5. customSolvents were removed under reduced pressure

Sources & evidence

ORD record
ord-7b54cf94915f4dfb8c875f28ccffe5d3
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Linked notes

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