Methyl 4-nitrobutyrate → N,N-Dimethyl-4-nitro-butyramide

HRID 1784341Notes

Reaction equation

HRID 1784341 reaction equation
[N+:1]([CH2:4][CH2:5][CH2:6][C:7]([O:9]C)=O)([O-:3])=[O:2].O.[CH3:12][NH:13][CH3:14]>CO>[CH3:12][N:13]([CH3:14])[C:7](=[O:9])[CH2:6][CH2:5][CH2:4][N+:1]([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 25604Methyl 4-nitrobutyrateHCID 27521Dimethylamine, hydrate

Product 1

HCID 29928540N,N-Dimethyl-4-nitro-butyramideYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-nitrobutyrate (1.0 g, 6.80 mmol) in methanol (10 ml) was added 40% dimethylamine water solution (12.5 ml, 102 mmol). The solution was stirred at room temperature for 48 h, concentrated by vacuum, and diluted with ethyl acetate (20 ml). The organic layer was dried and evaporated. The residue was purified by flash chromatography over silica gel (Hexane-EtOAc, 1:1) to give the title product (0.99 g, 91%). 1H NMR (CDCl3): 4.53 (t, J=6.6 Hz, 2H), 3.02-2.94 (m, 6H), 2.48-2.43 (m, 2H), 2.36-2.31 (m, 2H).

Workup

  1. concentrationconcentrated by vacuum
  2. additiondiluted with ethyl acetate (20 ml)
  3. customThe organic layer was dried
  4. customevaporated
  5. customThe residue was purified by flash chromatography over silica gel (Hexane-EtOAc, 1:1)

Sources & evidence

ORD record
ord-9d9377c9ba184aa9b5aa36b9512eb16a
Source dataset
uspto-grants-2009_03
Patent number
US07504382B2

Reaction notes

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