Preparation of heterocyclic fluorine compounds by the Schiemann reaction. III. Some monofluoroisoquinolines was written by Roe, Arthur;Teague, Claude E. Jr.. And the article was included in Journal of the American Chemical Society in 1951.Application of 394-67-2 This article mentions the following:
1-Aminoisoquinoline (15 g.) in 120 ml. 42% HBF4, cooled to -5°, the precipitate suspended in 150 ml. petr. ether (b. 30-40°), treated (1 hr.) at room temperature with 7.2 g. powd. NaNO2 and then 30 min. with EtONO, and kept 2 hrs., gives 36 g. 1-isoquinolinediazonium fluoborate (I), decompose 68°; decomposition of I gives 13% (overall) yield of 1-fluoroisoquinoline (II), b. 208°, n30D 1.5861. The following were prepared with variations of the above method: 3-isomer of I, m. 15-25°; of II, b. 251°, n30D 1.5875, 49%; 4-isomer of I, m. 20-5°; of II, b. 236°, n30D 1.5914, 36%; 5-isomer of I, m. 190°; of II, b62 145°, m. 43°, 67%. Of the 4 isomeric I, only the 1- and 5-isomers are stable; the 3- and 4-isomers decompose at room temperature The hydroxyisoquinolines, expected by-products in the Schiemann reaction, were isolated in every case from the reaction mixtures p-FC6H4CH:CHCH(OEt)2 and H2SO4 do not yield 6-fluoroisoquinoline. In the experiment, the researchers used many compounds, for example, 4-Fluoroisoquinoline (cas: 394-67-2Application of 394-67-2).
4-Fluoroisoquinoline (cas: 394-67-2) belongs to isoquinoline derivatives. The isoquinoline structure occurs in a considerable number of alkaloids in widely separated plant families. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Application of 394-67-2
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem