Methyl Acrylate → Methyl (E)-3-(6-methoxy-2-methyl-5-quinolinyl)-2-propenoate

HRID 655893Notes

Reaction equation

HRID 655893 reaction equation
Br[C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:14])=[N:7]2.[C:15]([O:19][CH3:20])(=[O:18])[CH:16]=[CH2:17]>>[CH3:13][O:12][C:11]1[C:2](/[CH:17]=[CH:16]/[C:15]([O:19][CH3:20])=[O:18])=[C:3]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:6]([CH3:14])[CH:5]=[CH:4]2

Participants

3

Reactant 2

HCID 7294Methyl AcrylateHCID 114252565-Bromo-6-methoxy-2-methylquinoline

Product 1

HCID 83766494Methyl (E)-3-(6-methoxy-2-methyl-5-quinolinyl)-2-propenoateYield 71%

Procedure

The title compound was prepared from 5-bromo-6-methoxy-2-methylquinoline (6b) and methyl acrylate using methods as described in the literature for similar compounds (Frank et al., 1978) in 71% yield. 1H NMR (DMSO-d6, HMDSO), δ: 2.63 (3H, s); 3.76 (3H, s); 4.01 (3H, s); 6.71 (1H, d, J=15.5 Hz); 7.43 (1H, d, J=8.5 Hz); 7.64 (1H, d, J=8.8 Hz); 8.02 (1H, d, J=8.8 Hz); 8.16 (1H, d, J=15.5 Hz); 8.42 (1H, d, J=8.5 Hz).

Sources & evidence

ORD record
ord-04f28f5f63914bb89f32399ce1a343ca
Source dataset
uspto-grants-2011_12
Patent number
US08071620B2

Reaction notes

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