Elimination of carbon monoxide by electron impact on quinolineN-oxide, carbostyril and 8-hydroxyquinoline

Abstract

Under electron impact, the molecular ions of quinoline N-oxide, carbostyril and 8-hydroxyquinoline lose carbon monoxide giving a fragment ion C8H7N (m/z 117), which was shown by collision-activated dissociation in each case to have the structure of the molecular ion of indole. Its formation from 8-hydroxyquinoline requires an unusual rearrangement. Isoquinoline N-oxide loses HCN rather than CO and gives a fragment which has the structure of the molecular ion of benzofuran. When the first three compounds were subjected to flash vacuum pyrolysis, quinoline N-oxide at 500–700°C gave carbostyril and indole was detected by gas chromatography/mass Spectrometry. At 900°C carbostyril and 8-hydroxyquinoline both gave indole in small amounts, detected by gas chromatography/mass Spectrometry.