Cyanoacetamide → HCID 178418929, compound

Reaction equation

C(O[C:4](=O)[CH2:5][C:6]([CH3:8])=[O:7])C.[C:10]([CH2:12][C:13]([NH2:15])=[O:14])#[N:11].P(Cl)(Cl)(Cl)=O>>[C:10]([C:12]1[C:13]([OH:14])=[N:15][CH:8]=[C:6]([OH:7])[C:5]=1[CH3:4])#[N:11]

Participants

Reactant 3

HCID 7898Cyanoacetamide

HCID 8868Ethyl Acetoacetate

HCID 24813Phosphorus oxychloride

Product 1

HCID 178418929HCID 178418929, compound

Procedure

Amine was generated by the condensation of ethylacetoacetate with cyanoacetamide followed by reaction with phosphorus oxychloride to provide 3-cyano-2,5-dihydroxy-4-methylpyridine. Hydrogenation with palladium dichloride gave the 3-cyano-4-methylpyridine which was hydrogenated with Raney nickel in ammonia and ethanol to afford the desired amine (J. Org. Chem. 1959, 25, 560.).

Sources & evidence

ORD record: ord-3a88dd9b299e453abb8cca072f727e81
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094909B2

Reaction notes

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