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Trichlorophenoxyacetic acid → 2-[2-(2,4,5-Trichloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester

HRID 1945432
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1945432
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[CH:19]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(OCC)(=O)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:6](=[O:8])[CH2:5][O:4][C:3]2[CH:9]=[C:10]([Cl:14])[C:11]([Cl:13])=[CH:12][C:2]=2[Cl:1])[CH:19]=1
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Komponenten

7

Edukt 4

HCID 1480Trichlorophenoxyacetic acidHCID 8857Ethyl AcetateHCID 236984Methyl 2-aminopyridine-4-carboxylateHCID 2724699PyBOP

Produkt 1

HCID 248120952-[2-(2,4,5-Trichloro-phenoxy)-acetylamino]-isonicotinic acid methyl esterAusbeute 24,45 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To solution of (2,4,5-trichloro-phenoxy)-acetic acid (150 mg, 0.59 mmol), 2-amino isonicotinic acid methyl ester (179 mg, 1.18 mmol) and DMAP (144 mg, 1.18 mmol) in DMF 13 mL was added PyBOP (614 mg, 1.18 mmol) at room temperature. Reaction mixture was stared at room temperature. Resulting mixture poured onto ice cold water, was diluted by ethyl acetate. The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:1) to give 2-[2-(2,4,5-trichloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester as a colorless solid (0.056 g, 24.45% yield).

Aufarbeitung

  1. customReaction mixture
  2. customwas stared at room temperature
  3. customResulting mixture
  4. additionpoured onto ice cold water
  5. customThe organic phase was separated
  6. washsequentially washed with aqueous sodium bicarbonate, brine and water
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-dd5790bf973b45f2954d627f426d14e2
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08394799B2

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