Ammonium Chloride → 3-(4-Amino-2,6-dichloro-phenoxy)-quinoline-8-carboxylic acid methyl ester

HRID 2422432Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422432
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([O:15][C:16]1[C:21]([Cl:22])=[CH:20][C:19]([N+:23]([O-])=O)=[CH:18][C:17]=1[Cl:26])=[CH:10]2)=[O:4].[NH4+].[Cl-]>CCO.C1COCC1.O.[Fe]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][C:11]([O:15][C:16]1[C:17]([Cl:26])=[CH:18][C:19]([NH2:23])=[CH:20][C:21]=1[Cl:22])=[CH:10]2)=[O:4]

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 574409423-(2,6-Dichloro-4-nitro-phenoxy)-quinoline-8-carboxylic acid methyl ester

Produkt 1

HCID 574409393-(4-Amino-2,6-dichloro-phenoxy)-quinoline-8-carboxylic acid methyl esterAusbeute 118,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 18504229Ethanol tetrahydrofuran waterLösungsmittel

Versuchsvorschrift

To a solution of 3-(2,6-Dichloro-4-nitro-phenoxy)-quinoline-8-carboxylic acid methyl ester (98) (1.26 mmol) and NH4Cl (370 mg, 6.91 mmol) in EtOH/THF/H2O=8 mL/4 mL/2 mL was added iron powder (386 mg, 6.91 mmol). The reaction mixture was refluxed for 3.5 h. After cooling to room temperature and insoluble materials were filtered by Celite filtration. The filtrate was concentrated and sat NaHCO3 was added to the residue, which was extracted twice with AcOEt. Organic layer was washed by brine, dried over MgSO4, and concentrated. Crude residue was purified by column chromatography (hexane/AcOEt=2/1, 80 g of silica gel) to afford compound 99 (543 mg). 1H NMR (300 MHz, DMSO-d6) δ 3.91 (3H, s), 5.77 (2H, br s), 6.78 (2H, s), 7.50 (1H, d, J=3.0 Hz), 7.61 (1H, dd, J=8.1 Hz), 7.81 (1H, dd, J=1.4, 6.4 Hz), 8.08 (1H, dd, J=1.4 Hz, 6.4 Hz), 8.93 (1H, d, J=3.0 Hz).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 3.5 h
  2. filtrationinsoluble materials were filtered by Celite filtration
  3. concentrationThe filtrate was concentrated
  4. additionwas added to the residue, which
  5. extractionwas extracted twice with AcOEt
  6. washOrganic layer was washed by brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customCrude residue was purified by column chromatography (hexane/AcOEt=2/1, 80 g of silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-6846984fc80549d38233169ed1467459
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960408B2

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