Ammonia → Ethyl 3-amino-2-ethylcrotonate

HRID 1508684Notes

Reaction equation

HRID 1508684 reaction equation
[CH2:1]([CH:3]([C:9](=O)[CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].C([O-])(=O)C.[NH4+:16].N.S([O-])([O-])(=O)=O.[Na+].[Na+]>CO>[NH2:16]/[C:9](/[CH3:10])=[C:3](/[CH2:1][CH3:2])\[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24436Sodium SulfateHCID 79065Butanoic acid, 2-ethyl-3-oxo-, ethyl esterHCID 517165Ammonium Acetate

Product 1

HCID 10630766Ethyl 3-amino-2-ethylcrotonateYield 93.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 100-mL round bottom flask was charged with ethyl 2-ethyl-3-oxo-butanoate (5 g, 90% purity, 28 mmol), ammonium acetate (22 g, 280 mmol, 10 eq.), ammonia (2N in EtOH, 14 ml, 1 eq.), anhydrous sodium sulfate (8 g, 56 mmol, 2 eq.) and MeOH (30 ml). The resulting mixture was stirred at room temperature overnight. The volatile material was removed under reduced pressure and the residue was treated with dichloromethane (40 ml). Insoluble material was removed by filtration and washed with dichloromethane (2×20 ml). The organics was washed with aqueous sodium bicarbonate, dried over Na2SO4. Removal of solvent gave ethyl (Z)-3-amino-2-ethyl-but-2-enoate (4.1 g, 82% yield) as a white solid.

Workup

  1. customThe volatile material was removed under reduced pressure
  2. additionthe residue was treated with dichloromethane (40 ml)
  3. customInsoluble material was removed by filtration
  4. washwashed with dichloromethane (2×20 ml)
  5. washThe organics was washed with aqueous sodium bicarbonate
  6. dry with materialdried over Na2SO4
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-68fe9a38924f426b9aab2dc7ff876524
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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