Ethanol → 2-(2-Methoxyphenyl)-1,10-Phenanthroline Hydrochloride Chloride

HRID 1395936

Reaktionsgleichung

Reaktionsgleichung von HRID 1395936
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[CH:8][CH:7]=[N:6]3)[N:3]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl-:1].[ClH:1].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[CH:8][CH:7]=[N:6]3)[N:3]=1

Komponenten

8

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 3551932-Chloro-1,10-phenanthrolineHCID 27339582-Methoxyphenylboronic acid

Produkt 1

HCID 866307712-(2-Methoxyphenyl)-1,10-Phenanthroline Hydrochloride Chloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Chloro-1,10-phenanthroline (5.9 g, 27.5 mMole), 2-methoxyphenylboronic acid (2) (5 g, 33 mMole), tetrakis(triphenylphosphine)palladium(0) (1 g, 0.825 mMole), 2M-Na2CO3 (33 mL, 66 mMole) and ethanol (8 mL) were suspended in toluene (70 mL) and heated to 100° C. with good stirring for 24 hours. At the end of this period the reaction was cooled, diluted with ethyl acetate (200 mL) and the aqueous layer run off. The organic layer was washed with water (3×100 mL) and intermittently with brine to break up any emulsion formed. The organic layer was filtered through a pad of celite, dried over MgSO4, filtered and concentrated to an oil. The oil was dissolved in CH2Cl2 (20 mL) and diethyl ether (150 mL) added. With good stirring, a 20% solution of concentrated HCl in ethanol (20 mL) was added. The yellow 2-(2-methoxyphenyl)-1,10-phenanthroline hydrochloride chloride was filtered off, washed with ether and air-dried. Yield 9.7 g.

Aufarbeitung

  1. temperatureAt the end of this period the reaction was cooled
  2. washThe organic layer was washed with water (3×100 mL) and intermittently with brine
  3. customformed
  4. filtrationThe organic layer was filtered through a pad of celite
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to an oil
  8. dissolutionThe oil was dissolved in CH2Cl2 (20 mL)
  9. additiondiethyl ether (150 mL) added
  10. additionWith good stirring, a 20% solution of concentrated HCl in ethanol (20 mL) was added
  11. filtrationThe yellow 2-(2-methoxyphenyl)-1,10-phenanthroline hydrochloride chloride was filtered off
  12. washwashed with ether
  13. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-2d144cb8cdd9424f82e12bf934b63356
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08900722B2

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