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

HRID 2075498Notes

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-22116be38d2e46a28dfd57073a36f7df
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919628B2

Reaction notes

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