Hydrochloric Acid → HCID 178517807, compound

HRID 2294535Notes

Reaction equation

Cl.[Cl:2][C:3]1(Cl)[CH2:8][C:7]([Cl:9])=[C:6]([Cl:10])[NH:5][C:4]1=[O:11]>>[Cl:2][C:3]1[C:4]([OH:11])=[N:5][C:6]([Cl:10])=[C:7]([Cl:9])[CH:8]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 21475315HCID 21475315, compound

Product 1

HCID 178517807HCID 178517807, compound

Procedure

U.S. Pat. No. 4,996,323 (Pews) discloses a process for preparing 3,5,6-trichloropyridin-2-ol by conducting the following three separate reactions: trichloroacetyl chloride is added to acrylonitrile in the presence of a catalytic amount of copper or a cuprous salt to produce 2,2,4-trichloro-4-cyanobutanoyl chloride; the 2,2,4-trichloro-4-cyanobutanoyl chloride is cyclized by contacting it with acidic reagents, preferably in an anhydrous state, to form 3,3,5,6-tetrachloro-3,4-dihydropyridin-2-one; and hydrogen chloride can be eliminated from this dihydropyridinone compound to yield 3,5,6-trichloropyridin-2-ol in an aromatization reaction. However, the dihydropyridinone compound can alternatively split off water to yield 2,3,5,6-tetrachloropyridine. The water produced as a by-product during formation of the 2,3,5,6-tetrachloropyridine is a major contributor to yield loss via numerous side reactions.

Sources & evidence

ORD record: ord-2206679305b94caea678864aa62641ce
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688953

Reaction notes

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