Methanamine, N-methoxy-, hydrochloride (1:1) → 2,6-Dichloro-N-methoxy-N-methylpyridine-3-carboxamide

HRID 30095

Reaktionsgleichung

Reaktionsgleichung von HRID 30095
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].F[P-](F)(F)(F)(F)F.[N:19]1([O:28][C:29](N(C)C)=[N+](C)C)[C:23]2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CNOC>CN(C)C=O.O>[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([N:19]([O:28][CH3:29])[CH3:23])=[O:5]

Komponenten

8

Edukt 5

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 8540472,6-Dichloronicotinic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 534034112,6-Dichloro-N-methoxy-N-methylpyridine-3-carboxamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2,6-dichloronicotinic acid (500 mg, 2.63 mmol, Aldrich 90%) in anhydrous N,N-dimethylformamide (5 mL) were added O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.28 g, 3.37 mmol, Aldrich), 1-hydroxybenzotriazole hydrate (456 mg, 3.37 mmol, Aldrich) followed by N,N-diisopropylethylamine (1.3 g, 10.0 mmol) and N,O-dimethylhydroxylamine hydrochloride (306 mg, 3.15 mmol, Aldrich) at 0° C. The reaction was stirred for 1-2 hrs, treated with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and concentrated. The crude product was purified on silica gel with hexanes/ethyl acetate to give 2,6-Dichloro-N-methoxy-N-methyl-nicotinamide as a white solid (304.5 mg, 50% yield). HRMS, observed: 233.9968, Calcd for M+: 233.9963

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified on silica gel with hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1b00b34e51a549dc9e5341edcc4b3b6e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423051B2

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