Synthesis of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

Preparation of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

Alternative Names: EEDQ; 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline; Ethyl 2-ethoxyquinoline-1(2H)-carboxylate; 1-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline;

Preparation of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

Preparation of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

A solution of 155 ml (1.0 mole) of triethylamine in 92 ml (2.0 mole) absolute alcohol is added at -5 °C to a mixture of 97 ml (1.0 mole) ethyl chloroformate and 130 g (1.0 mole) of quinoline in 300 ml of dry benzene. After stirring for 1 hour, the contents of the flask are washed with water and the aqueous layer is extracted several times with chloroform, dried with magnesium sulfate and chloroform is removed in vacuo. The obtained oily is treated with 20 ml of ether and the solidified colorless product is filtered off, washed with cold ether and dried. The yield of N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline is 140 g (57%), m.p. 63.5-65 °C. After keeping the mother liquor in the refrigerator overnight an additional crop (25 g) is obtained. Overall yield 165 g (66%).

Fieser’s Reagents for Organic Synthesis, v. 5, 236, (1970)

IUPAC Name

ethyl 2-ethoxy-2H-quinoline-1-carboxylate

InChI

InChI=1S/C14H17NO3/c1-3-17-13-10-9-11-7-5-6-8-12(11)15(13)14(16)18-4-2/h5-10,13H,3-4H2,1-2H3

InChI Key

GKQLYSROISKDLL-UHFFFAOYSA-N

Canonical SMILES

CCOC1C=CC2=CC=CC=C2N1C(=O)OCC

MeSH Synonyms

BC 681, EEDQ, N-carbethoxy-2-ethoxy-1,2-dihydroquinoline, N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline

Depositor-Supplied Synonyms

EEDQ, 16357-59-8, N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline, 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline, ethyl 2-ethoxyquinoline-1(2H)-carboxylate, 1-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline, ethyl 2-ethoxy-2H-quinoline-1-carboxylate, 2-Ethoxy-1(2H)-quinolinecarboxylic acid, ethyl ester, BC 681, NSC 147831, MLS000069601, 1(2H)-QUINOLINECARBOXYLIC ACID, 2-ETHOXY-, ETHYL ESTER, GKQLYSROISKDLL-UHFFFAOYSA-N, EINECS 240-418-2, Ethyl 1,2-dihydro-2-ethoxyquinoline-1-carboxylate, BRN 0533048, SMR000059033, Ethyl 2-ethoxy-1,2-dihydro-1-quinolinecarboxylate, ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate, 2-ethoxy-2h-quinoline-1-carboxylic acid ethyl ester, Ethyl N-(2-ethoxy-1,2-dihydroquinoline)carboxylate, ethyl 2-ethoxy-1,2-dihydroquinolinecarboxylate, PubChem19586, N-carbethoxy-2-ethoxy-1,2-dihydroquinoline, SCHEMBL338, ACMC-209dq0, cid_27833, KSC496S8H, 149837_ALDRICH, AC1L1E27, Jsp003284, CHEMBL1527785, BDBM40545, C14H17NO3, CTK3J6983, GKQLYSROISKDLL-UHFFFAOYSA-, MolPort-002-317-341, BB_SC-5595, HMS1776O14, ANW-22054, BBL011113, CE-125, NSC147831, SBB057548, STK802369, WLN: T66 BN CHJ BVO2 CO2, AKOS001075463, AKOS016842289, AC-2881, LS40941, MCULE-9556592165, NSC-147831, RP28777, RTR-007020, NCGC00246989-01, AK-33574, AN-13547, BR-33574, HE003641, HE215503, KB-23606, P495, SC-11258, SY003226, Ethyl 2-ethoxy-1(2H)-quinolinecarboxylate, 1-carbethoxy-2-ethoxy-1,2-dihydroquinoline, 1-carbethoxy-2-ethoxy-l,2-dihydroquinoline, AB1001554, DB-019159, LS-141631, TL8001251, TR-007020, AM20050163, E0363, FT-0606405, ST24030515, ST50308466, 2-ethoxy-1-ethoxycarbonyl-1,2dihydroquinoline, 2-ethoxy-1-ethoxycarbonyl-1.2-dihydroquinoline, 2-ethoxy-l-ethoxycarbonyl-1,2-dihydroquinoline, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline, Y-8785, 5-21-03-00028 (Beilstein Handbook Reference), ethyl 1,2-dihydro-2-ethoxy-1-quinolinecarboxylate, ethyl-2-ethoxy-1,2-dihydroquinoline-1-carboxylate, 2-ethoxy-1(2H)-quinolinecarboxylic acid ethyl ester, T5334899, 2-ethoxy- 1(2H)-quinolinecarboxylic acid ethyl ester, 2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), 3B1-001953, 3B3-012970, EEDQ (2-Ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline), (3Z)-3-(ethoxy-hydroxymethylidene)-1-methylquinoline-2,4-dione, InChI=1/C14H17NO3/c1-3-17-13-10-9-11-7-5-6-8-12(11)15(13)14(16)18-4-2/h5-10,13H,3-4H2,1-2H3

Removed Synonyms

CID27833, 1(2H)-Quinolinecarboxylic acid, ethyl ester, C000470

Share This

Leave a Reply

Your email address will not be published. Required fields are marked *