Methyl propiolate → HCID 178515908, compound

HRID 594769Notes

Reaction equation

HRID 594769 reaction equation
[NH2:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[C:9](OC)(=[O:12])[C:10]#[CH:11]>>[OH:12][C:9]1[CH:10]=[CH:11][C:3]2[C:4](=[O:8])[CH2:5][CH2:6][CH2:7][C:2]=2[N:1]=1

Participants

3

Reactant 2

HCID 13536Methyl propiolateHCID 788923-Aminocyclohex-2-en-1-one

Product 1

HCID 178515908HCID 178515908, compoundYield 21.3%

Procedure

A mixture of 3-amino-2-cyclohexen-1-one (25.0 g, 224.9 mmol) and methyl propiolate (23.6 g, 281 mmol) was heated to reflux for 1 h. The mixture was cooled and the solid was collected by filtration, washing with THF, to give 7.8 g (21%) of the title compound as a yellow solid. [M+H] calc'd for C9H9NO2, 164. found 164.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. temperatureThe mixture was cooled
  4. filtrationthe solid was collected by filtration
  5. washwashing with THF

Sources & evidence

ORD record
ord-31cfd2d3979a4d3182a82b2b1fc54f72
Source dataset
uspto-grants-2016_01
Patent number
US09242968B2

Reaction notes

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