Ammonia → Ethyl 3-amino-hex-2-enoate

HRID 1422106Notes

Reaction equation

HRID 1422106 reaction equation
O=[C:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH3:12].S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)C>[NH2:12][C:2]([CH2:9][CH2:10][CH3:11])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24083Sulfuric acid magnesium salt (1:1)HCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 85320704Ethyl 3-amino-hex-2-enoateYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 3-oxo-hexanoate (100 g, 0.63 mmol) was dissolved in 400 ml of diethyl ether and ammonia was bobbled through the solution for 8 hours. During the reaction magnesium sulfate was added in portions as a drying agent. When no starting material was detected on TLC, the mixture was filtered, and the solvent was evaporated to afford 75 g (76%) of ethyl 3-amino-hex-2-enoate as an oil. 1H--NMR (CDCl3, 200 MHz) δ: 0.95 (t, 3 H); 1.25 (t, 3 H); 1.58 (sextet, 2 H); 2.09 (t, 2 H); 4.11 (q, 2 H); 4.52 (s, 1 H).

Workup

  1. additionwas added in portions as a drying agent
  2. filtrationthe mixture was filtered
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-16299a109fac4d10ac50eb70f66612ad
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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