Methyl Ethyl Ketone → HCID 15917386, Verbindung

HRID 1758139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758139
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[N:6][CH:7]=1.Cl[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>CCCCCC.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=2)=[N:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 15917385HCID 15917385, Verbindung

Produkt 1

HCID 15917386HCID 15917386, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A mixture of 1.5 grams (0.0068 mole) 2-(5-chloropyridin-2-yloxy)phenol, 1.3 grams 2-chloro-5-nitropyridine, 1.0 grams potassium carbonate, and 40 ml of methyl ethyl ketone was heated at reflux overnight. Excess water was added and the aqueous mixture extracted with 200 ml of ethyl ether. The ether extract was washed with saturated NaHCO3, H2O, brine, dried (MgSO4), filtered, and the solvent was evaporated to yield a solid which was suspended in hexane and filtered. Yield 1.4 grams, m.p. 82°-84°; ir (Nujol): 6.15, 6.25 (C=N, NO2), 13.30 (broad), 13.70 microns; NMR (CDCl3): δ6.55 (s, ArH), 6.75 (d, ArH), 6.95 (s, ArH), 7.35 (s, 4H, ArH), 7.40-7.65 (m, ArH), 8.05 (d, ArH), 8.40 (AB quartet, ArH), 8.95 (d, ArH).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. extractionthe aqueous mixture extracted with 200 ml of ethyl ether
  4. extractionThe ether extract
  5. washwas washed with saturated NaHCO3, H2O, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customto yield a solid which
  10. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-5643838a8404401792cf6a0047268d03
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04371736

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