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A convenient preparation of 1,4‐dihydro‐1‐methyl‐4‐oxo‐2‐quinolinecarboxaldehyde from N ‐methylisatoic anhydride
Author(s) -
Coppola Gary M.
Publication year - 1986
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.5570230623
Subject(s) - chemistry , manganese , aldehyde , alcohol , hydroxymethyl , organic chemistry , medicinal chemistry , catalysis
The dianion of hydroxyacetone is readily generated with LDA in THF at ‐65°. This dianion reacts rapidly with N ‐methylisatoic anhydride ( 6 ) at ‐65° to furnish 2‐hydroxymethyl‐1‐methylquinolin‐4(1 H )‐one ( 12 ). The alcohol is oxidized to aldehyde 4 with manganese dioxide, and is subsequently converted to α,β ‐unsaturated ester 5 under Horner‐Emmons conditions.