Potassium Carbonate → HCID 66818891, compound

HRID 1024670Notes

Reaction equation

[C:1](=[O:4])([O-])[O-].[K+].[K+].Cl[C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[C:10](Cl)[N:9]=1.[C:18]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)#[N:19]>CN(C=O)C>[C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:8]2[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[C:10]([O:4][C:1]3[CH:24]=[CH:25][C:20]([C:18]#[N:19])=[CH:21][CH:22]=3)[N:9]=2)=[CH:22][CH:21]=1)#[N:19]

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium carbonate (2.09 g, 15.1 mmol) was added to a stirred solution of 2,6-Dichloro-3-nitro pyridine (1.0 g, 5.3 mmol), dissolved in 10 ml of DMF, at a temperature of 5° C. The flask was stirred for 10 min at the same temperature. 4-Cyano phenol (1.26 g, 10.6 mmol), dissolved in 5 ml of DMF was added dropwise to the reaction mixture over a period of 10 min and the flask was heated to 80° C. for 10-12 h. The reaction mixture was poured into ice-cold water and the product was extracted with 250 ml of ethyl acetate. Ethyl acetate layer was washed with water and brine solution. The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 1.35 g of the required 2,6-Bis-(4-cyano phenoxy)-3-nitro pyridine which was used in the next step without further purification. 1H NMR (DMSO-d6): δ 7.06 (1H, d), 7.32 (4H, dd), 7.82 (411, t), 8.74 (1H, d).

Workup

additionwas added dropwise to the reaction mixture over a period of 10 min
additionThe reaction mixture was poured into ice-cold water
extractionthe product was extracted with 250 ml of ethyl acetate
washEthyl acetate layer was washed with water and brine solution
dry with materialThe organic layer was dried over anhydrous sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a9e1925d995842cca5f0175c3a1499cd
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722930B2

Reaction notes

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