Synthesis of 8-aminoquinoline

Preparation of 8-aminoquinoline

Preparation of 8-aminoquinoline

Preparation of 8-aminoquinoline

A mixture of 34.8 g. of 8-nitroquinoline, 0.25 g. of Adams platinic oxide catalyst, 150 ml. of ethyl acetate, 25 ml. of absolute ethanol, and 25 ml. of ether is agitated in the presence of hydrogen. In 1.5 hours 3 molar equivalents of hydrogen are absorbed. The resulting solution of the 8-aminoquinoline is treated with activated carbon and distilled to give 27.6 g. (96%) of 8-aminoquinoline, b.p. 140.5-141.5°/7 mm., m.p. 62.5-63.5°. One recrystallization from a mixture of ether and hexane gives product melting at 64-65°.

J. Am. Chem. Soc., 62, 1644 (1940).

IUPAC Name

quinolin-8-amine

InChI

InChI=1S/C9H8N2/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H,10H2

InChI Key

WREVVZMUNPAPOV-UHFFFAOYSA-N

Canonical SMILES

C1=CC2=C(C(=C1)N)N=CC=C2

MeSH Synonyms

8-((6-(diethylamino)hexyl)amino)-6-methoxy-4-methylquinoline, 8-(6-diethylaminohexylamino)-6-methoxy-4-methylquinoline dihydrochloride, 8-aminoquinoline, 8-quinolinamine, N,N-diethyl-N’-(6-methoxy-4-methyl-8-quinolinyl)-1,6- hexanediamine, sitamaquine, WR 006026, WR 6026, WR-006026, WR-6026, WR006026, WR6026

Depositor-Supplied Synonyms

8-AMINOQUINOLINE, quinolin-8-amine, 578-66-5, 8-Quinolinamine, 8-Quinolylamine, Quinoline, 8-amino-, quinolin-8-ylamine, 8-amino quinoline, CCRIS 1683, WREVVZMUNPAPOV-UHFFFAOYSA-N, NSC 7933, EINECS 209-427-9, AS-232, NC 066, WR 6920, BRN 0114474, 8-amino-quinoline, quinolin-8-yl-amine, PubChem7574, ACMC-1AZ9V, UNII-U34EAV21TG, AC1L1X6P, AC1Q51CD, U34EAV21TG, cid_11359, KSC269S5B, BIDD:GT0148, CHEMBL99932, SCHEMBL159694, 260789_ALDRICH, AC1Q52B7, BDBM32144, CTK1G9950, WREVVZMUNPAPOV-UHFFFAOYSA-, NSC7933, MolPort-000-514-611, BB_SC-5230, ZINC105176, ACT08349, NSC-7933, ANW-32815, BBL008000, RW2006, SBB004126, STK344576, WTI-10868, ZINC00105176, 5330-29-0 (di-HCl), AKOS000108492, MCULE-9280410958, PS-5383, RP01413, RTC-062235, SDCCGMLS-0065843.P001, NCGC00184185-01, NCGC00184185-02, AJ-11163, AK-35724, AN-21475, BP-13199, BR-35724, CJ-00757, HE000829, KB-46634, SC-05481, ZB003542, AB1007160, DB-012217, LS-141301, ST2419059, ST4082204, TC-062235, WT-130276, 4CH-015487, 8-Quinolinamine, 9CI; 8-N-Methanesulfonyl, A0419, AM20050982, BB 0221197, FT-0080378, FT-0621492, TL80073502, EN300-10405, M-4137, MLS-0065843.0001, AB00375631-02, 5-22-10-00316 (Beilstein Handbook Reference), A831646, AC-907/25014399, J-200081, W-206848, 3B3-001897, A3000/0126362, InChI=1/C9H8N2/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H,10H2, Q8A

Removed Synonyms

8-Aminoisoquinoline, Quipazine dimaleate, isoquinolin-8-amine, CID11359, CA-432, 23687-27-6, 1000340-19-1, 10374-76-2, 5786-68-5

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