Pyridine → HCID 15058670, compound

HRID 1087892Notes

Reaction equation

HRID 1087892 reaction equation
[F:1][CH2:2][CH2:3][O:4][C:5]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:6]=1C=O.OC1C=CC(C=O)=C[C:18]=1[N+:25]([O-])=O.Cl.NO.N1C=CC=CC=1.[Se](=O)=O>C(Cl)(Cl)Cl.C(O)C>[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[CH:9][C:10]([C:18]#[N:25])=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14]

Participants

8

Reactant 5

HCID 1049PyridineHCID 181694-Hydroxy-3-nitrobenzaldehydeHCID 24007Selenium DioxideHCID 443297Hydroxyamine hydrochlorideHCID 22164151HCID 22164151, compound

Product 1

HCID 15058670HCID 15058670, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

In a manner similar to Sosnovsky et al. (Synthesis, p 722, (1979)), the reaction of 3.0 grams (0.014 mole) of -(2-fluoroethoxy)-3-nitrobenzaldehyde (prepared by the method of Example 1 from 4-hydroxy-3-nitrobenzaldehyde), 1.1 gram (0.015 mole) of hydroxylamine hydrochloride, and 1.2 ml (0.014 mole) of pyridine (dissolved in 10 ml of chloroform) in 50 ml of chloroform and ethanol (70/30 mixture) followed by treatment with 1.6 gram (0.014 mole) of selenium dioxide yielded 2.3 grams of 4-cyano-2-nitrophenyl 2-fluoroethyl ether as a solid.

Workup

  1. customIn a manner similar to Sosnovsky et al. (Synthesis, p 722, (1979))

Sources & evidence

ORD record
ord-57fdb8b757264b1985e31005c8010523
Source dataset
uspto-grants-1990_10
Patent number
US04960884

Reaction notes

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