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

HRID 1698528Notes

Reaction equation

HRID 1698528 reaction equation
Cl[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].[CH3:15][NH2:16]>O1CCCC1>[CH3:15][NH:16][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

4

Reactant 2

HCID 6329MethylamineHCID 10751184Methyl 2-chloro-3-nitrobenzoate

Product 1

HCID 59635415Benzoic acid, 2-(methylamino)-3-nitro-, methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 21.5 g (99.5 mmol) of methyl 2-chloro-3-nitrobenzoate in 300 mL of tetrahydrofuran (THF) was treated with drop wise addition of 300 mL (597 mmol) of methylamine (2M solution in THF) and was stirred overnight at room temperature. The reaction was concentrated to dryness, dissolved in dichloromethane, and washed with aqueous sodium bicarbonate and water. The organics were dried over sodium sulfate, filtered, and concentrated in vacuo to give 20.8 g (100%) of the title compound.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. dissolutiondissolved in dichloromethane
  3. washwashed with aqueous sodium bicarbonate and water
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-749a808ba22c4faca68f4875942b2870
Source dataset
uspto-grants-2012_04
Patent number
US08163935B2

Reaction notes

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