Methylamine → N-Methyl-4-Nitro-Butyramide

HRID 1784337Notes

Reaction equation

HRID 1784337 reaction equation
[N+:1]([CH2:4][CH2:5][CH2:6][C:7]([O:9]C)=O)([O-:3])=[O:2].[CH3:11][NH2:12]>>[CH3:11][NH:12][C:7](=[O:9])[CH2:6][CH2:5][CH2:4][N+:1]([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 25604Methyl 4-nitrobutyrate

Product 1

HCID 55299464N-Methyl-4-Nitro-ButyramideYield 98%

Procedure

To a sealed reaction vessel was added methyl 4-nitrobutyrate (1.00 g, 6.80 mmol) and methylamine (2.0 M methylamine in MeOH, 50.0 mL, 100 mmol). The resulting yellow solution was stirred at room temperature for 20 h. The solvent was evaporated and the residue was purified by flash chromatography (silica gel, load: CH2Cl2, elution with EtOAc:Hexanes, 1:1) to give the title product (0.97 g, 98%) as a white solid. 1H NMR (CDCl3): 5.84 (br s, NH, 1H), 4.54-4.48 (m, 2H), 2.82 (d, J=4.7 Hz, 3H), 2.36-2.32 (m, 4H).

Workup

  1. customTo a sealed reaction vessel
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash chromatography (silica gel, load: CH2Cl2, elution with EtOAc:Hexanes, 1:1)

Sources & evidence

ORD record
ord-cd198af0bccc46ceba3df9a587ad8e88
Source dataset
uspto-grants-2009_03
Patent number
US07504382B2

Reaction notes

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