Ethyl cyanoacetate → 2-cyano-N-cyclopropylacetamide

HRID 2375591Notes

Reaction equation

[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[C:5]([CH2:7][C:8](OCC)=[O:9])#[N:6]>>[C:5]([CH2:7][C:8]([NH:4][CH:1]1[CH2:3][CH2:2]1)=[O:9])#[N:6]

Participants

Reactant 2

HCID 7764Ethyl cyanoacetate

HCID 69828Cyclopropylamine

Product 1

HCID 21678842-cyano-N-cyclopropylacetamideYield 100.1%

Conditions

Temperature: 45 °C

Procedure

To a flask charged with cyclopropylamine (12.3 g, 215.3 mmol) was added ethyl cyanoacetate (9.8 g, 86.1 mmol). The reaction was stirred at 45° C. for 1.5 hour, cooled and concentrated under reduced pressure to give 10.7 g title compound (˜100%) as a light yellow solid. 1H NMR (300.132 MHz, CDCl3) δ 6.20 (bs, 1H), 3.34 (s, 2H), 2.75 (m, 2H), 0.83 (m, 2H), 0.59 (m, 2H).

Workup

temperaturecooled
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c16dda6195a34199b3d1e666760e29a9
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465795B2

Reaction notes

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