Dimethyl acetylenedicarboxylate → HCID 619331, compound

HRID 326633Notes

Reaction equation

HRID 326633 reaction equation
[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[CH3:10][O:11][C:12]([C:14]#[C:15][C:16](OC)=[O:17])=[O:13]>>[CH3:1][S:2][C:3]1[CH:9]=[C:8]2[C:6](=[CH:5][CH:4]=1)[NH:7][C:14]([C:12]([O:11][CH3:10])=[O:13])=[CH:15][C:16]2=[O:17]

Participants

3

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 660384-(Methylthio)aniline

Product 1

HCID 619331HCID 619331, compoundYield 28.5%

Procedure

Using the method described in Example 18a with 4-methylthioaniline (20 g) and dimethyl-acetylene dicarboxylate (20.21 g) as reagents gave methyl 6-methylthio-4-oxo-1,4-dihydroquinoline-2-carboxylate (10.12 g), m.p. 264°-266° C. δ (360 MHz, DMSO-d6), 2.55 (3H, s, CH3S), 3.96 (3H, s, CH3O), 6.68 (1H, s, 3-H), 7.64 (1H, dd, 7-H), 7.83 (1H, d, 5-H) and 7.89 (1H, d, 8-H).

Sources & evidence

ORD record
ord-56a1b27f46624b4c8cd90c8c4c749775
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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