Pyridine → Methyl 3-(2-bromoacetamido)crotonate

HRID 56134Notes

Reaction equation

HRID 56134 reaction equation
[NH2:1]/[C:2](/[CH3:8])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5].N1C=CC=CC=1.[Br:15][CH2:16][C:17](Br)=[O:18]>C(Cl)Cl>[Br:15][CH2:16][C:17]([NH:1]/[C:2](/[CH3:8])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5])=[O:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 643918Methyl 3-aminocrotonate

Product 1

HCID 90023822Methyl 3-(2-bromoacetamido)crotonateYield 15.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

A mixture of methyl 3-aminocrotonate (3.20 g, 27.79 mmol) and pyridine (2.64 g, 33.33 mmol) in CH2Cl2 (60 mL) was stirred at −20° C. for 20 min. To the mixture was added a solution of bromoacetyl bromide (5.61 g, 27.79 mmol) in CH2Cl2 (20 mL) dropwise. The mixture was stirred at rt for 2 h. The organic phase was washed with brine (100 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=5:1) to give the title compound as a reddish solid (0.99 g, 15%).

Workup

  1. stirringThe mixture was stirred at rt for 2 h
  2. washThe organic phase was washed with brine (100 mL×3)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=5:1)

Sources & evidence

ORD record
ord-f0808efa167f40b5a72b52f2f65ca3c8
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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