2-[(2-Chloro-4-nitrophenoxy)methyl]-6-methylpyridine → 3-Chloro-4-[(6-methylpyridin-2-yl)methoxy]aniline

HRID 222036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 222036
[Cl:1][C:2]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:16]=[C:15]([CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[N:7]=1)[NH2:17]

Komponenten

4

Edukt 1

HCID 668773902-[(2-Chloro-4-nitrophenoxy)methyl]-6-methylpyridine

Produkt 1

HCID 220552383-Chloro-4-[(6-methylpyridin-2-yl)methoxy]anilineAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

2-[(2-chloro-4-nitrophenoxy)methyl]-6-methylpyridine (4.87 g, 17.5 mmol) and iron powder (4.87 g, 87.4 mmol) were mixed in 150 mL acetic acid, and were stirred at rt overnight. The reaction mixture was filtered through a pad of Celite®, and washed with EtOAc. The filtrate was concentrated in vacuo and neutralized with saturated Na2CO3 solution. The contents were extracted with EtOAc (5×300 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The resulting crude material was triturated with Hex/EtOAc (2:1) to afford 3-chloro-4-[(6-methylpyridin-2-yl)methoxy]aniline (3.84 g, 88%) as a white solid. 1H-NMR (DMSO) δ 7.70 (dd, 1H), 7.31 (d, 1H), 7.17 (d, 1H), 6.88 (d, 1H), 6.65 (d, 1H), 6.44 (dd, 1H), 5.01 (s, 2H), 4.93 (s, 2H), 2.46 (s, 3H); LCMS RT=0.25 min; [M+H]+=249.2.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo
  4. extractionThe contents were extracted with EtOAc (5×300 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting crude material was triturated with Hex/EtOAc (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-c1e1ad8661e743c0b5e9fa4b91a3d4e5
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207172B2

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