Ethyl 2-methylacetoacetate → HCID 178431789, compound

HRID 1168556Notes

Reaction equation

[CH3:1][CH:2]([C:6]([CH3:8])=O)[C:3]([NH2:5])=[O:4].CC(C(C)=O)C(OCC)=O.[OH-].[NH4+].[C:21]([CH2:23][C:24]([O:26]CC)=O)#[N:22]>>[NH4+:5].[OH:26][C:24]1[C:23]([C:21]#[N:22])=[C:6]([CH3:8])[C:2]([CH3:1])=[C:3]([OH:4])[N:5]=1

Participants

Reactant 4

HCID 701Ethyl 2-methylacetoacetate

HCID 7764Ethyl cyanoacetate

HCID 14923Ammonium Hydroxide

HCID 3614092HCID 3614092, compound

Product 1

HCID 178431789HCID 178431789, compoundYield 90%

Procedure

2-methylacetoacetamide 2, made from ethyl 2-methylacetoacetate 1 by reaction with ammonium hydroxide for six days (at about 60% yield), is reacted with ethyl cyanoacetate 4 over four days to produce 2,6-dihydroxy-4,5-dimethyl-3-pyridinecarbonitrile, ammonium salt 5 (90% yield). The ammonium salt is hydrolyzed with hydrobromic acid and decarboxylated. The excess hydrobromic acid is evaporated to dryness followed by filtration of ammonium bromide after taking up the 2,6-dihydroxy-3,4-dimethylpyridine hydrobromide salt 6 in absolute ethyl alcohol. The ethyl alcohol is evaporated to dryness and the residue is heated with water and potassium hydroxide to isolate 2,6-dihydroxy-3,4-dimethylpyridine (70% yield).

Sources & evidence

ORD record: ord-732eecd596d249d18ad22a05bfaf907b
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06624307B1

Reaction notes

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