Lithium iodide → 4-(6-Cyano-5-hydroxy-pyridin-2-yl)-benzoic acid ethyl ester

HRID 983415Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[C:13]([C:19]#[N:20])[N:12]=2)=[CH:7][CH:6]=1)[CH3:2].[Li+].[I-]>N1C(C)=CC(C)=CC=1C>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([C:19]#[N:20])[N:12]=2)=[CH:9][CH:10]=1)[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A solution of 4-(6-cyano-5-methoxy-pyridin-2-yl)-benzoic acid ethyl ester from Example 13d in collidine is treated with LiI and heated at 120° C. for 24 h. The reaction mixture is evaporated, the residue is taken into water and neutralized with 1 N HCl. The resulting precipitate is collected and dried to give 4-(6-cyano-5-hydroxy-pyridin-2-yl)-benzoic acid ethyl ester.

Workup

customThe reaction mixture is evaporated
customThe resulting precipitate is collected
customdried

Sources & evidence

ORD record: ord-da5589dd4c5e468882903486c4d0c31f
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864267B2

Reaction notes

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