Phenol → 4-(O-Benzylhydroxylamino)-3-methoxy-2-methylpyridine

HRID 1417743

Reaktionsgleichung

Reaktionsgleichung von HRID 1417743
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10].C1(O)C=CC=CC=1.[CH2:18]([O:25][NH2:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+]>C(Cl)Cl>[CH2:18]([O:25][NH:26][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

6

Edukt 4

HCID 996PhenolHCID 14798Sodium HydroxideHCID 102313O-BenzylhydroxylamineHCID 105830464-Chloro-3-methoxy-2-methylpyridine

Produkt 1

HCID 152793584-(O-Benzylhydroxylamino)-3-methoxy-2-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

16 g of 4-chloro-3-methoxy-2-methylpyridine, 63 g of phenol and 40 g of O-benzylhydroxylamine are stirred at 120° C. under nitrogen for 4 hours. After cooling, the mixture is shaken with 500 ml of 2N NaOH and CH2Cl2. The aqueous phase is extracted a second time with CH2Cl2. After concentrating the combined CH2Cl2 phases, excess O-benzylhydroxylamine is distilled off in vacuo at 0.6 mm. The residue crystallizes on stirring with hexane. After filtering off with suction and washing with hexane 21.6 g=88.4% of product remain. The product is recrystallized from ethyl acetate. M.p.: 130° C.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionThe aqueous phase is extracted a second time with CH2Cl2
  3. concentrationAfter concentrating the combined CH2Cl2 phases, excess O-benzylhydroxylamine
  4. distillationis distilled off in vacuo at 0.6 mm
  5. customThe residue crystallizes
  6. filtrationAfter filtering off with suction
  7. washwashing with hexane 21.6 g=88.4% of product
  8. customThe product is recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c4bb313083bb4d4583811c567400dcf4
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05877322

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