Diethyl acetylenedicarboxylate → HCID 19735208, compound

Participants

Reaction Steps

Treatment of 3-iodo-5-methylaniline (4.1 g) with diethylacetylene dicarboxylate (2.8 ml) as described in Example 1b, gave a mixture (3.0 g) of ethyl 5-iodo-7-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate [δ (360 MHz, DMSO-d6) 1.50 (3H, t, CH2CH3), 2.76 (3H, s, CH3), 4.41 (2H, q, CH2CH3), 6.58 (1H, s, 3-H), 7.74 (1H, s, 6-H) and 7.78 (1H, s, 8-H)] and ethyl 7-iodo-5-methyl-4-oxo-1,4-dihydroquinoline-2-carboxylate [δ (360 MHz, DMSO-d6) 1.33 (3H, t, CH2CH3), 2.72 (3H, s, CH3), 4.41 (2H, q, CH2CH3), 6.54 (1H, bs, 3-H), 7.40 (1H, s, 6-H) and 8.20 (1H, s, 8-H)].

Provenance & Evidence