Alkyl nitrate nitration of active methylene compounds. Nitration of 1‐methyl4‐piperidone, 1‐methyl‐2‐pyrrolidinone and 1,3‐dimethyl‐2‐pyrrolidinone | Zendy

Feuer Henry | Zendy; Blecker Lamarr R. | Zendy; Jans Robert W. | Zendy; Frost John W. | Zendy

Premium

Alkyl nitrate nitration of active methylene compounds. Nitration of 1‐methyl4‐piperidone, 1‐methyl‐2‐pyrrolidinone and 1,3‐dimethyl‐2‐pyrrolidinone

Author(s) -

Feuer Henry,

Blecker Lamarr R.,

Jans Robert W.,

Frost John W.

Publication year - 1979

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570160314

Subject(s) - nitration , chemistry , yield (engineering) , medicinal chemistry , ring (chemistry) , methylene , nitro , potassium nitrate , alkyl , nitrate , potassium , organic chemistry , materials science , metallurgy

The reaction of 1‐methyl‐4‐piperidone ( 1 ) with amyl nitrate in the potassium tert ‐butoxidetetrahydrofuran system gave dipotassium 5‐methyl‐2‐oxo‐1,3‐piperidinedinitronate ( 4 ) in 78% yield. Similar treatment of 1‐methyl‐2‐pyrrolidinone ( 2 ) afforded potassium 3‐methyl‐2‐oxopyrrolidinenitronate ( 7 ) in 85% yield. In contrast, the nitration of 1,3‐dimethyl‐2‐pyrrolidinone ( 3 ) led to opening of the lactam ring with the formation of amyl 2‐aza‐2‐methyl‐5‐nitrohexanoate ( 10 ) in 40% yield. Acidification of disalt 4 did not cause ring opening but gave the dipolar ion of 1‐methyl‐3‐nitro 4‐hydroxy‐5‐ aci ‐nitro‐Δ 3 ‐tetrahydropyridinium (6).

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research