Synthesis of quinoline

Preparation of quinoline

Alternative Names: 1-Azanaphthalene; 1-Benzazine; Chinoline; Chinolin;

Preparation of quinoline

Preparation of quinoline

24 g nitrobenzene, 38 g aniline, 120 g glycerine, and 100 g concentrated sulfuric acid are cautiously mixed in a flask of 1-liter capacity, and heated together under reflux condenser, until the reaction just begins. If the flame is removed this does not proceed too vigorously. When it is finished the liquid is kept boiling for two hours longer, then it is diluted with water, and the nitrobenzene distilled off in steam. The solution is rendered alkaline with sodium hydroxide and again distilled with steam. The distillate contains quinoline and aniline. To remove aniline the mixture is treated with an excess of hydrochloric acid, and sodium nitrite is then added until the smell of nitrous acid persists even on shaking ; the solution is heated to boiling until all the diazobenzene is destroyed (i.e. till the evolution of gas has ceased). The liquid now made alkaline again with caustic soda and distilled with steam. The distillate is extracted with ether; the ether is evaporated and the residual quinoline dried with solid caustic potash and distilled. Yield about 40 g. Boiling point 237° C.

Introduction to the preparation of organic compounds, E. Fisher, 108-109, 1909

IUPAC Name

quinoline

InChI

InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H

InChI Key

SMWDFEZZVXVKRB-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)C=CC=N2

MeSH Synonyms

quinoline, quinoline hydrochloride

Depositor-Supplied Synonyms

QUINOLINE, 91-22-5, 1-Azanaphthalene, 1-Benzazine, Chinoline, Chinolin, Quinolin, Benzo[b]pyridine, Benzopyridine, Chinoleine, Leucol, Leukol, 2,3-Benzopyridine, Benzo(b)pyridine, USAF EK-218, B 500, NSC 3396, 1-Benzine, Chinolin [Czech], CCRIS 547, FEMA No. 3470, HSDB 121, Benzopyridine (VAN), CHEBI:17362, UN2656, CHEMBL14474, UNII-E66400VT9R, AI3-01241, B-500, SMWDFEZZVXVKRB-UHFFFAOYSA-N, EINECS 202-051-6, DSSTox_CID_1798, DSSTox_RID_76332, DSSTox_GSID_21798, CAS-91-22-5, benzazabenzene, benzazine, 3-Benzopyridine, 8-quinolinyl, ACMC-20aimg, AC1L1NVV, Quinoline (8CI,9CI), Epitope ID:140096, SCHEMBL2774, C9H7N, NCIOpen2_007906, WLN: T66 BNJ, MLS002303065, BIDD:ER0666, SCHEMBL483852, W347000_ALDRICH, 241571_ALDRICH, 530-64-3 (hydrochloride), SCHEMBL1193639, SCHEMBL3311562, SCHEMBL8571823, NSC3396, Quinoline [UN2656] [Poison], MolPort-000-883-590, BB_SC-6766, E66400VT9R, HMS2271F08, Quinoline [UN2656] [Poison], NSC-3396, STR01546, Tox21_201478, Tox21_300068, ANW-75062, BBL011390, BDBM50047015, SBB060379, STL146493, ZINC00896153, AKOS000119139, LS-1919, MCULE-2825394284, RP19862, RTC-063626, UN 2656, NCGC00091190-01, NCGC00091190-02, NCGC00091190-03, NCGC00091190-04, NCGC00254119-01, NCGC00259029-01, AJ-24226, AK-98665, AN-42551, CJ-04486, HE019500, HE355080, HE411917, KB-60280, SC-47591, SMR000112309, ZB015074, DB-057248, ST2413766, TC-063626, FT-0602839, FT-0633705, Q0011, Q0085, ST51046569, 5730-EP2269978A2, 5730-EP2269985A2, 5730-EP2269989A1, 5730-EP2269991A2, 5730-EP2270000A1, 5730-EP2270004A1, 5730-EP2270008A1, 5730-EP2270010A1, 5730-EP2270113A1, 5730-EP2270505A1, 5730-EP2272517A1, 5730-EP2272537A2, 5730-EP2272813A2, 5730-EP2272828A1, 5730-EP2272832A1, 5730-EP2272837A1, 5730-EP2272843A1, 5730-EP2272849A1, 5730-EP2272935A1, 5730-EP2272972A1, 5730-EP2272973A1, 5730-EP2274983A1, 5730-EP2275395A2, 5730-EP2275401A1, 5730-EP2275409A1, 5730-EP2275411A2, 5730-EP2275412A1, 5730-EP2277858A1, 5730-EP2277872A1, 5730-EP2277877A1, 5730-EP2280000A1, 5730-EP2280009A1, 5730-EP2280013A1, 5730-EP2281563A1, 5730-EP2281815A1, 5730-EP2281817A1, 5730-EP2281818A1, 5730-EP2281824A1, 5730-EP2284150A2, 5730-EP2284151A2, 5730-EP2284152A2, 5730-EP2284153A2, 5730-EP2284155A2, 5730-EP2284156A2, 5730-EP2284157A1, 5730-EP2284158A1, 5730-EP2284159A1, 5730-EP2284164A2, 5730-EP2284169A1, 5730-EP2284174A1, 5730-EP2284920A1, 5730-EP2285800A1, 5730-EP2287140A2, 5730-EP2287148A2, 5730-EP2287150A2, 5730-EP2287155A1, 5730-EP2287161A1, 5730-EP2287162A1, 5730-EP2287165A2, 5730-EP2287166A2, 5730-EP2289871A1, 5730-EP2289877A1, 5730-EP2289890A1, 5730-EP2289891A2, 5730-EP2289892A1, 5730-EP2292586A2, 5730-EP2292590A2, 5730-EP2292592A1, 5730-EP2292593A2, 5730-EP2292601A1, 5730-EP2292602A1, 5730-EP2292603A1, 5730-EP2292604A2, 5730-EP2292611A1, 5730-EP2292617A1, 5730-EP2292618A1, 5730-EP2292620A2, 5730-EP2292630A1, 5730-EP2293650A1, 5730-EP2295419A2, 5730-EP2295421A1, 5730-EP2295429A1, 5730-EP2295432A1, 5730-EP2295433A2, 5730-EP2298305A1, 5730-EP2298731A1, 5730-EP2298732A1, 5730-EP2298737A1, 5730-EP2298739A1, 5730-EP2298740A1, 5730-EP2298741A1, 5730-EP2298746A1, 5730-EP2298750A1, 5730-EP2298755A1, 5730-EP2298756A1, 5730-EP2298761A1, 5730-EP2298763A1, 5730-EP2298767A1, 5730-EP2298770A1, 5730-EP2298771A2, 5730-EP2298776A1, 5730-EP2299785A1, 5730-EP2301536A1, 5730-EP2301538A1, 5730-EP2301544A1, 5730-EP2301912A2, 5730-EP2301913A1, 5730-EP2301914A1, 5730-EP2301916A2, 5730-EP2301918A1, 5730-EP2301920A1, 5730-EP2301923A1, 5730-EP2301930A1, 5730-EP2301933A1, 5730-EP2301937A1, 5730-EP2305219A1, 5730-EP2305250A1, 5730-EP2305254A1, 5730-EP2305637A2, 5730-EP2305640A2, 5730-EP2305643A1, 5730-EP2305648A1, 5730-EP2305649A1, 5730-EP2305651A1, 5730-EP2305652A2, 5730-EP2305658A1, 5730-EP2305668A1, 5730-EP2305677A1, 5730-EP2305688A1, 5730-EP2305695A2, 5730-EP2305696A2, 5730-EP2305697A2, 5730-EP2305698A2, 5730-EP2305808A1, 5730-EP2306788A1, 5730-EP2306789A1, 5730-EP2308510A1, 5730-EP2308562A2, 5730-EP2308832A1, 5730-EP2308838A1, 5730-EP2308840A1, 5730-EP2308843A1, 5730-EP2308848A1, 5730-EP2308849A1, 5730-EP2308850A1, 5730-EP2308854A1, 5730-EP2308861A1, 5730-EP2308863A1, 5730-EP2308882A1, 5730-EP2308926A1, 5730-EP2309564A1, 5730-EP2311455A1, 5730-EP2311796A1, 5730-EP2311797A1, 5730-EP2311798A1, 5730-EP2311799A1, 5730-EP2311825A1, 5730-EP2311826A2, 5730-EP2311827A1, 5730-EP2311842A2, 5730-EP2314558A1, 5730-EP2314575A1, 5730-EP2314576A1, 5730-EP2314583A1, 5730-EP2314587A1, 5730-EP2315303A1, 5730-EP2315502A1, 5730-EP2316452A1, 5730-EP2316459A1, 5730-EP2316470A2, 5730-EP2316832A1, 5730-EP2316833A1, 5730-EP2316905A1, 5730-EP2316906A2, 5730-EP2371810A1, 5730-EP2371811A2, 5730-EP2371812A1, 5730-EP2371831A1, 5730-EP2372804A1, 5730-EP2378585A1, C06413, M-7415, AE-641/01960007, I14-93758, 3B3-029906, InChI=1/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7, 20214-07-7

Removed Synonyms

Leucoline, Cinch, Quinoline hydrochloride, CID7047, ZINC01706876, ACN-032347, C037219

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