Diethyl acetylenedicarboxylate → HCID 19735208, compound

HRID 326648Notes

Reaction equation

[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5].[CH2:10]([O:12][C:13]([C:15]#[C:16][C:17](OCC)=[O:18])=[O:14])[CH3:11].IC1C=C2C(C(=O)C=C(C(OCC)=O)N2)=C(C)C=1>>[I:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:4]2[C:3]=1[C:17](=[O:18])[CH:16]=[C:15]([C:13]([O:12][CH2:10][CH3:11])=[O:14])[NH:5]2

Participants

Reactant 3

HCID 69803Diethyl acetylenedicarboxylate

HCID 19735205HCID 19735205, compound

HCID 197352133-Iodo-5-methylaniline

Product 1

HCID 19735208HCID 19735208, compound

Procedure

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)].

Sources & evidence

ORD record: ord-cb1e391c358049c7b3e6e3cb8c4335ea
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05270309

Reaction notes

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