Synthesis of 8-nitroquinoline

Preparation of 8-nitroquinoline

Preparation of 8-nitroquinoline

Preparation of 8-nitroquinoline

100 g of conc. sulphuric add and 51.5 g of arsenic acid are well shaken in a flask with 110 gms. glycerine and 50 g of o-nitroaniline and then carefully heated on a sand bath under a reflux condenser. As soon as the reaction begins, the flask is removed from the sand bath until it has moderated; it is then boiled for 3 hours. When cold, a large volume of water is added to the contents of the flask, and the whole allowed to stand overnight, and then filtered. Sodium hydroxide is carefully added to the filtrate until a brown precipitate appears, which is filtered off and discarded. Sodium hydroxide is then added to the filtrate until alkaline. The 8-nitroquinoline thus obtained is washed with water, boiled up with alcohol and animal charcoal, and after filtration is precipitated by the addition of water. Yield 55%, colourless monoclinic needles; insoluble in water; soluble in alcohol; m.p. 88° C.

Systematic organic chemistry, by W. M. Cumming, 166-167, 1937.

IUPAC Name

8-nitroquinoline

InChI

InChI=1S/C9H6N2O2/c12-11(13)8-5-1-3-7-4-2-6-10-9(7)8/h1-6H

InChI Key

OQHHSGRZCKGLCY-UHFFFAOYSA-N

Canonical SMILES

C1=CC2=C(C(=C1)[N+](=O)[O-])N=CC=C2

Depositor-Supplied Synonyms

8-NITROQUINOLINE, 607-35-2, Quinoline, 8-nitro-, CCRIS 457, HSDB 5092, NSC 346, OQHHSGRZCKGLCY-UHFFFAOYSA-N, EINECS 210-135-9, BRN 0135178, AI3-08912, NSC346, 8-Nitroqunioline, 8-Nitro-quinoline, zlchem 249, PubChem5825, ACMC-209mls, DSSTox_CID_985, 8-NITRO QUINOLINE, UNII-YWO6S88V4V, AC1L1Y8C, DSSTox_RID_75907, YWO6S88V4V, DSSTox_GSID_20985, WLN: T66 BNJ JNW, KSC355A1H, ARONIS25148, SCHEMBL949962, 130273_ALDRICH, CHEMBL167727, CTK2F5013, NSC-346, ZLC0058, MolPort-000-368-864, BB_SC-0273, ZINC334909, ACT05937, Tox21_200683, ANW-33566, BBL005523, SBB066322, STK801629, ZINC00334909, AKOS000277126, AC-2532, LS-7562, MCULE-6713363771, RP02850, RTC-062236, TRA0015149, VQ10384, 8-Nitro-quinolin;Quinoline, 8-nitro-;, NCGC00248797-01, NCGC00258237-01, AJ-19693, AK-25209, AN-13901, BR-25209, CAS-607-35-2, CJ-02903, HE001634, KB-46906, SC-05674, U377, ZB010760, AB1001259, DB-031637, TC-062236, FT-0621571, N0345, ST24030041, ST45024375, A26303, M-4088, AB00443675-03, AJ-333/25006054, W-105230, W-203269, 3B3-009675, InChI=1/C9H6N2O2/c12-11(13)8-5-1-3-7-4-2-6-10-9(7)8/h1-6, 2ZQ

Removed Synonyms

null, CID11830, 5-20-07-00327 (Beilstein Handbook Reference), 183208-38-0

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