HCID 10476733, compound → HCID 67788575, compound

HRID 1757279Notes

Reaction equation

HRID 1757279 reaction equation
[CH2:1]([C:4]1[CH:13]=[C:12]([O:14]CC2C=CC(C3C(C(O)=O)=CC=CC=3)=CC=2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:2][CH3:3].C(C1C=C(OCC2C=CC(C3C(C(OC)=O)=CC=CC=3)=CC=2)C2C(=CC=CC=2)N=1)CC>CS(C)=O>[CH2:1]([C:4]1[CH2:13][C:12](=[O:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 10476733HCID 10476733, compoundHCID 11741515HCID 11741515, compound

Product 1

HCID 67788575HCID 67788575, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(Example 3): 4'-[(2-Propylquinolin-4-yloxy)methyl]biphenyl-2-carboxylic acid*, m.p. 198°-200° C.; NMR (d6 -DMSO): 0.97(t,3H), 1.8(m,2H), 2.85(t,2H), 5.43(s,2H), 7.08(s,1H), 7.35-7.65(complex m,8H), 7.73(dt,2H),7.87(d,1H), 8.15(dd,1H), 12.7(br s,1H); mass spectrum (-ve FAB, DMSO/GLY): 396 (M-H)-, 186; microanalysis, found: C,77.5; H,6.0; N,3.5%; C26H23NO3.0.33C2H5OH requires: C,77.8; H,6.1; N,3,4%; starting from methyl 4'-[(2-propylquinolin-4-yloxy)methyl]biphenyl-2-carboxylate, obtained as a viscous oil; NMR: 1.03(t,3H), 1.87(m,2H), 2.94(t,2H), 3.68(s,3H), 5.36(s,2H), 6.75(s,1H), 7.34-7.6(complex m,8H), 7.68(dt,1H), 7.85(dd,21H), 8.03(d, 1H), 8.25(dd,1H); 13C NMR (CDCl3): (benzylic CH2) 69.8; itself obtained from 2-propyl-4-quinolone using analogous procedures to those described in Example 1; [*Note: 1M aqueous citric acid solution was used in place of 2M hydrochloric acid in the work-up procedure].

Workup

  1. customobtained as a viscous oil

Sources & evidence

ORD record
ord-cfe6f151c7344cf3aed96d9c504bdf71
Source dataset
uspto-grants-1995_08
Patent number
US05444071

Reaction notes

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