Potassium Iodide → 1-(6-Chloro-pyridin-3-ylmethoxy)-naphthalene-2-carboxylic acid methyl ester

HRID 2062066Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[OH:15])=[O:4].CN(CC1C=C(CN(C)C)C(O)=C(CN(C)C)C=1)C.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+].[Cl:43][C:44]1[CH:49]=[CH:48][C:47]([CH2:50]Cl)=[CH:46][N:45]=1>O>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]=1[O:15][CH2:50][C:47]1[CH:46]=[N:45][C:44]([Cl:43])=[CH:49][CH:48]=1)=[O:4]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1.0 g 1-hydroxy-2-naphthoic acid methyl ester in 20 ml abs. DMF 3.22 g cesium carbonate was added, followed by addition of 0.16 g potassium iodide and 0.96 g 2-chloro-5-chloromethyl-pyridine. Under argon-atmosphere the reaction mixture was heated to 60° C. for 1 h. The mixture was then poured into water and extracted with ethyl acetate at pH9 three times. The combined organic layers were dried over magnesium sulphate, filtrated and after removal of the solvent a crude product was obtained which was recrystallized from diethyl ether to yield 1.62 g 1-(6-chloro-pyridin-3-ylmethoxy)-naphthalene-2-carboxylic acid methyl ester.

Workup

extractionextracted with ethyl acetate at pH9 three times
dry with materialThe combined organic layers were dried over magnesium sulphate
filtrationfiltrated
customafter removal of the solvent a crude product
customwas obtained which
customwas recrystallized from diethyl ether

Sources & evidence

ORD record: ord-33fe749da4b24e059f4e1b5fa4b0c7ba
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283479B2

Reaction notes

Loading…