Methylamine → Methyl 3-(methylamino)but-2-enoate

HRID 2276006Notes

Reaction equation

HRID 2276006 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[CH3:9][NH2:10]>O>[CH3:9][NH:10][C:3]([CH3:5])=[CH:2][C:1]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 7757Methyl acetoacetate

Product 1

HCID 2734182Methyl 3-(methylamino)but-2-enoateYield 80.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl acetoacetate (23.2 g, 0.2 mol) in water (15 mL) at 10° C. was added dropwise methylamine (40% aqueous solution, 18.6 g, 0.24 mol). The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The resulting solid precipitate was collected by filtration and washed with ice water (2×), and then dried in a vacuum oven at 55° C. overnight to provide the title compound as a white solid (20.9 g).

Workup

  1. filtrationThe resulting solid precipitate was collected by filtration
  2. washwashed with ice water (2×)
  3. customdried in a vacuum oven at 55° C. overnight

Sources & evidence

ORD record
ord-bb0b147d5baf433082f876fa9ffcd8f4
Source dataset
uspto-grants-2015_09
Patent number
US09131693B2

Reaction notes

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