Acetic Anhydride → 4-Ethoxy-3-(4-pyridyl)-3-buten-2-one

HRID 2417647Notes

Reaction equation

HRID 2417647 reaction equation
[CH3:1][C:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)=[O:3].[CH:11](OCC)(OCC)[O:12][CH2:13][CH3:14].C(OC(=O)C)(=O)C>C(O)(=O)C>[CH3:1][C:2]([C:4]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)=[CH:11][O:12][CH2:13][CH3:14])=[O:3]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 805524-Pyridinylacetone

Product 1

HCID 30212274-Ethoxy-3-(4-pyridyl)-3-buten-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The process according to claim 2 where 4-pyridinylmethyl methyl ketone is first reacted with triethyl orthoformate, acetic anhydride and acetic acid to produce 2-ethoxy-1-(4-pyridinyl)ethenyl methyl ketone, said latter ketone is reacted with cyanoacetamide in the presence of at least a molar equivalent quantity of sodium hydroxide per mole of cyanoacetamide in methanol and the reaction mixture is neutralized to produce 1,2-dihydro-6-methyl-2-oxo-5-(4-pyridinyl)nicotinonitrile.

Sources & evidence

ORD record
ord-f0df5abe32624c84a5778ee775c05f02
Source dataset
uspto-grants-1984_09
Patent number
US04469871

Reaction notes

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