Water → HCID 19082078, compound

HRID 963302Notes

Reaction equation

[Cl:1][C:2]1[C:3]([CH2:19][CH3:20])=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:28]1[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][N:29]=1.O>CN(C)C=O.C1(C)C=CC(S([O-])=O)=CC=1.[Na+]>[Cl:1][C:2]1[C:3]([CH2:19][CH3:20])=[N:4][CH:5]=[CH:6][C:7]=1[NH:8][C:9](=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:28]2[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][N:29]=2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

0.59 g (2 mmol) of N-(3-chloro-2-ethylpyridin-4-yl)-4-hydroxyphenylacetamide, 0.32 g (2.2 mmol) of potassium carbonate, 0.35 g (2.2 mmol) of 2-chloro-5-nitropyridine and 0.01 g of sodium 4-toluenesulfinate were dissolved in 5 ml of N,N-dimethylformamide, and the solution was stirred for 50 minutes at 80° C. After completion of the reaction, the reaction solution was poured into water and extracted twice with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate) to obtain 0.5 g of the desired product as a milky white powder (melting point: 128° to 131° C.).

Workup

customAfter completion of the reaction
extractionextracted twice with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationThen, ethyl acetate was distilled off under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record: ord-0dfa572634bd47d9967fc1eee7411b8d
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05763463

Reaction notes

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