Lithium iodide → 2-[2-(4-tert-butyl-phenoxy)acetylamino]-isonicotinic Acid

HRID 1945439Notes

Reaction equation

C[O:2][C:3](=[O:25])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][C:11](=[O:24])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[CH:5]=1.[I-].[Li+]>N1C=CC=CC=1>[C:20]([C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:11]([NH:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][N:7]=2)[C:3]([OH:25])=[O:2])=[O:24])=[CH:15][CH:16]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

Conditions

Temperature: 125 °C

Procedure

To solution of 2-[2-(4-tert-butyl-phenoxy)-acetylamino]-isonicotinic acid methyl ester (51.8 mg, 0.15 mmol) in pyridine 6 ml was added lithium Iodide (12.6 mg, 0.30 mmol), and stirred at 125° C. Reaction mixture was concentrated, and purified by Prep-TLC(CH2Cl2:MeOH=10:1) to give as a colorless solid (394 mg, 77.94% yield).

Workup

customReaction mixture
concentrationwas concentrated
custompurified by Prep-TLC(CH2Cl2:MeOH=10:1)

Sources & evidence

ORD record: ord-9dcc5298cd7f4ac8a594878732af41ee
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394799B2

Reaction notes

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