HCID 10251829, compound → HCID 67689610, compound

HRID 1757280Notes

Reaction equation

HRID 1757280 reaction equation
[CH2:1]([C:5]1[CH:14]=[C:13]([O:15]CC2C=CC(C3C(C(O)=O)=CC=CC=3)=CC=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4].C(C1C=C(OCC2C=CC(C3C(C(OC)=O)=CC=CC=3)=CC=2)C2C(=CC=CC=2)N=1)CCC>CS(C)=O>[CH2:1]([C:5]1[CH2:14][C:13](=[O:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 10251829HCID 10251829, compoundHCID 10364310HCID 10364310, compound

Product 1

HCID 67689610HCID 67689610, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(Example 4): 4'-[(2-Butylquinolin-4-yloxy)methyl]biphenyl-2-carboxylic acid, m.p. 148° C.; NMR (d6 -DMSO): 0.93(t,3H), 1,38(m,2H), 1.8(m,2H), 2.95(t,2H), 5.5(s,2H), 7.25(s,1H), 7.33-7.68(complex m,8H), 7.7-7.85(m,2H), 7.98(d,1H), 8.2(d,1H); mass spectrum (-ve FAB, DMSO/GLY): 410 (M-H)-, 200; microanalysis found: C,77.1; H,6.1; N,3.1%; C27H25NO3.0.5H2O requires: C,77.1; H,6.2; N,3.3%; starting from methyl 4'-[(2-butylquinolin-4-yloxy)methyl]biphenyl-2-carboxylate obtained as viscous oil; NMR: 0.97(t,3H), 1.45(m,2H), 1.78(m,2H), 2.94(t,2H), 3.68(s,3H), 5.35(s,2H), 6.76(s,1H), 7.35-7.6(complex m,8H), 7.69(dt,1H), 7.88(dd,1H), 8.0 (d,1H), 8.25(dd,1H); mass spectrum (+ve CI): 426 (M+H)+, 225, 202; itself obtained from 2-butyl-4-quinolone using analogous procedures to those described in Example 1.

Workup

  1. customobtained as viscous oil

Sources & evidence

ORD record
ord-754d81c941894f30827d44233bc5c895
Source dataset
uspto-grants-1995_08
Patent number
US05444071

Reaction notes

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