Structure of 40106-98-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 40106-98-7 |
Formula : | C9H5ClN2O2 |
M.W : | 208.60 |
SMILES Code : | O=[N+](C1=C2C(Cl)=CC=NC2=CC=C1)[O-] |
MDL No. : | MFCD09261099 |
InChI Key : | DWKLLQSQXXCSEW-UHFFFAOYSA-N |
Pubchem ID : | 12582845 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16%; 59% | With sulfuric acid; nitric acid; at -15 - 20℃; for 3.0h; | a. 4-Chloro-8-nitroquinoline (6a) and 4-chloro-5-nitroquinoline (6d). 4-Chloroquinoline (10.0 g, 61.3 mmol) was added in small portions to sulfuric acid (45 mL) taking care to maintain the temperature at or below [15 C.] Then the solution was cooled and maintained at-5 C during the addition of fuming nitric acid (9 mL). The mixture was allowed to warm to room temperature and stirred for an additional 3 h. The reaction mix was poured on ice and basified (pH 9) with NH40H. The resulting precipitate was filtered, washed well with water, dried, and recrystallized from methanol to provide 7.5 g (59%) [OF 6A] as golden-brown needles; mp [128-129 C] (lit. 32 mp [129-130 C) ; IH NMR (CDC13)] [6] 7.67 (d, 1H, [J=4.] 5), 7.75 (dd, 1H, [J=8.] 6,. [J=7.] 6), 8.10 (dd, 1H, [J=7.] 6, [J=1.] 3), 8. 48 (dd, 1H, [J=8.] 6, J=1. 3), 8.94 (d, 1H, J=4. 5); [13C] NMR (CDC13) [6] 123.0, 124.4, 126.5, 127.5, 128.3, 140.6, 143.2, 148.7, 152.1. The mother liquor was evaporated and chromatographed in 19: 1 hexanes-ethyl acetate, to provide 2.05 g (16%) of the 5-nitro isomer 6d as a very light yellow solid; mp [144-146 C] (lit. 31 mp [150 C) ; IH] NMR (CDCl3) [6] 7.65 (d, 1H, J=4. 7), 7. 82 [(M,] 2H), 8.35 (dd, [1H,] [J=2.] 5, J=7. 3), 8.90 (d, 1H, J=4. 7); [13C] NMR [(CDC13)] 8 118.2, 123.4, 125.1, 128.8, 134.2, 135.6, 139.1, 149.7, 151.2. |