Diethyl acetylenedicarboxylate → HCID 19735179, compound

HRID 326644Notes

Reaction equation

HRID 326644 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([I: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].ClC1C=C2C(C(=O)C=C(C(OCC)=O)N2)=C(I)C=1>>[Cl:1][C:2]1[CH:8]=[C:7]([I: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

4

Reactant 3

HCID 69803Diethyl acetylenedicarboxylateHCID 151684493-Chloro-5-iodoanilineHCID 19735168HCID 19735168, compound

Product 1

HCID 19735179HCID 19735179, compound

Procedure

Treatment of 3-chloro-5-iodoaniline (1.4 g) with diethylacetylene dicarboxylate (0.93 ml), as described in Example 1b, gave a mixture (1.83 g) of ethyl 5-chloro-7-iodo-4-oxo-1,4-dihydroquinoline-2-carboxylate [δ (360 MHz, DMSO-d6) 1.37 (3H, t, CH2CH3), 4.40 (2H, q, CH2CH3), 6.59 (1H, s, 3-H), 7.61 (1H, s, 6-H), 8.32 (1H, s, 8-H) and 11.90 (1H, bs, NH)] and ethyl 7-chloro-5-iodo-4-oxo-1,4-dihydroquinoline-2-carboxylate [δ (360 MHz, DMSO-d6) 1.37 (3H, t, CH2CH3), 4.40 (2H, q, CH2CH3), 6.63 (1H, s, 3-H), 7.90 (1H, s, 6-H), 8.04 (1H, s, 8-H) and 11.90 (1H, bs, NH)].

Sources & evidence

ORD record
ord-6f8a3c6832234967a481b6f026c1e6cc
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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