Diethyl acetylenedicarboxylate → HCID 19735198, compound

HRID 326640Notes

Reaction equation

HRID 326640 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH2:9][CH3:10])[CH:8]=1)[NH2:5].[CH2:11]([O:13][C:14]([C:16]#[C:17][C:18](OCC)=[O:19])=[O:15])[CH3:12]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:6]([C:18](=[O:19])[CH:17]=[C:16]([C:14]([O:13][CH2:11][CH3:12])=[O:15])[NH:5]2)=[C:7]([CH2:9][CH3:10])[CH:8]=1

Participants

3

Reactant 2

HCID 69803Diethyl acetylenedicarboxylateHCID 19735171HCID 19735171, compound

Product 1

HCID 19735198HCID 19735198, compound

Procedure

Reaction of 3-chloro-5-ethylaniline (0.9 g) with diethylacetylene dicarboxylate (0.93 ml) as described in Example 1b gave a mixture of the two 5,7-regioisomers (800 mg). The isomers were separated by silica chromatography to give ethyl 7-chloro-5-ethyl-4-oxo-1,4-dihydroquinoline-2 -carboxylate (250 mg), mp 222°-3° C.; δ (360 MHz, DMSO-d6) 1.15 (3H, t, CH2CH3), 1.36 (3H, t, CO2CH2CH3), 3.25 (2H, q, CH2CH3), 4.42 (2H, q, CO2CH2) 6.57 (1H, s, 3-H), 7.12 (1H, d, 8-H), 7.87 (1H, d, 6-H) and 11.75 (1H, bs, NH); and ethyl 5-chloro-7-ethyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (200 mg), mp 182°-3° C.; δ (360 MHz, DMSO-d6) 1.21 (3H, t, CH2CH3), 1.35 (3H, t, CO2CH2CH3), 2.67 (2H, q, CH2CH3), 4.40 (2H, q, CO2CH2) 6.56 (1H, s, 3-H), 7.28 (1H, d, 6-H), 7.73 (1H, d, 8-H) and 11.78 (1H, bs, NH).

Workup

  1. customgave
  2. additiona mixture of the two 5,7-regioisomers (800 mg)
  3. customThe isomers were separated by silica chromatography

Sources & evidence

ORD record
ord-6919f228579342d69149f8a9ffc4e4e3
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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