Methyl propiolate → HCID 20253644, compound

HRID 638201Notes

Reaction equation

HRID 638201 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[CH:10]=[C:11]([CH3:13])[NH2:12])=[CH:5][CH:4]=1)#[N:2].[C:15](OC)(=[O:18])[C:16]#[CH:17]>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:10]2[CH:17]=[CH:16][C:15](=[O:18])[NH:12][C:11]=2[CH3:13])=[O:14])=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 13536Methyl propiolateHCID 70354444HCID 70354444, compound

Product 1

HCID 20253644HCID 20253644, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

was prepared following the procedure described in Example A-2 using 24.3 g of 3-(4-cyanophenyl)-1-methyl-3-oxo-1-propenamine, 12.5 ml of methyl propiolate and 100 ml of dimethylformamide. After a refluxing period of 24 hours, the reaction mixture was cooled whereupon the product precipitated, was collected, washed with ethanol and dried in a vacuum oven at 90° C. There was thus obtained 12.2 g of product, m.p. 267°-269° C., which was recrystallized from dimethylformamide using decolorizing charcoal, washed with ethanol and dried in a vacuum oven at 90° C. to yield 7.4 g of 5-(4-cyanobenzoyl)-6-methyl-2(1H)-pyridinone, m.p. 268°-270° C.

Workup

  1. customwas prepared
  2. temperaturethe reaction mixture was cooled whereupon the product
  3. customprecipitated
  4. customwas collected
  5. washwashed with ethanol
  6. customdried in a vacuum oven at 90° C
  7. customwas recrystallized from dimethylformamide using
  8. washwashed with ethanol
  9. customdried in a vacuum oven at 90° C.

Sources & evidence

ORD record
ord-179f88a53d6d46f79862e6edb6050482
Source dataset
uspto-grants-1985_12
Patent number
US04560691

Reaction notes

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