Ethyl Acetoacetate → Ethyl 3-(cyclopropylamino)but-2-enoate

HRID 250248Notes

Reaction equation

HRID 250248 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[CH:10]1([NH2:13])[CH2:12][CH2:11]1>>[CH2:8]([O:7][C:1](=[O:6])[CH:2]=[C:3]([NH:13][CH:10]1[CH2:12][CH2:11]1)[CH3:5])[CH3:9]

Participants

3

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 69828Cyclopropylamine

Product 1

HCID 67271584Ethyl 3-(cyclopropylamino)but-2-enoateYield 94%

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl acetoacetate (5.00 mL, 39.3 mmol) and cyclopropylamine (3.27 mL, 47.1 mmol) is stirred at 40° C. for 3 h. The mixture is concentrated under high vacuum overnight to give the title compound (6.23 g, 94%) of the as an oil, which is used without further purification in the next reaction.

Workup

  1. concentrationThe mixture is concentrated under high vacuum overnight

Sources & evidence

ORD record
ord-88a338c2ff4a4068bc812b77f288017c
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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