Oxalyl chloride → 2-[4-(6,7-Dimethoxyquinolin-4-yloxy)phenyl]acetyl chloride

HRID 1009742Notes

Reaction equation

HRID 1009742 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][CH:13]=[C:12]2[O:21][C:22]1[CH:27]=[CH:26][C:25](CC(O)=O)=[CH:24][CH:23]=1>C(Cl)(Cl)Cl>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][CH:13]=[C:12]2[O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:1][C:2]([Cl:4])=[O:3])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 596475402-(4-(6,7-Dimethoxyquinolin-4-yloxy)phenyl)acetic acid

Product 1

HCID 866288292-[4-(6,7-Dimethoxyquinolin-4-yloxy)phenyl]acetyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Oxalyl chloride (0.5 ml) was added dropwise to a stirred suspension of 2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetic acid (0.2 g) in chloroform (5 ml) at ambient temperature under argon. The resultant mixture was heated to reflux for 30 minutes. The mixture was evaporated to leave 2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetyl chloride as a solid. Chloroform (5 ml) and 5-amino-3-methyl-1,2,4 oxadiazole (0.099 g) were added in turn. Pyridine (0.286 ml) was added and the reaction mixture was stirred at ambient temperature for 16 hours. The solvent was evaporated and the residue was purified by preparative HPLC using a Waters ‘Xterra’ reversed-phase column (5 microns silica, 30 mm diameter, 250 mm length) that was eluted with decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. There was thus obtained the title compound (0.053 g); 1H NMR: (DMSOd6) 2.26 (s, 3H), 3.86 (s, 2H), 3.92 (s, 3H), 3.95 (s, 3H), 6.46 (d, 1H), 7.24 (d, 2H), 7.4 (s, 1H), 7.44 (d, 2H), 7.49 (s, 1H), 8.48 (d, 1H), 11.27 (br s, 1H); Mass Spectrum: M+H+ 421.

Workup

  1. temperatureto reflux for 30 minutes
  2. customThe mixture was evaporated

Sources & evidence

ORD record
ord-3f2eca7fd4324ef08ca169592d079e53
Source dataset
uspto-grants-2011_07
Patent number
US07973164B2

Reaction notes

Loading…