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Ammonium Chloride → 2-Cyclopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid ethyl ester

HRID 1753906
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1753906
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:10][C:11]=1[CH3:12])=[O:5])[CH3:2].[CH:20]1([Mg]Br)[CH2:22][CH2:21]1.[Cl-].[NH4+]>O1CCCC1.CN1CCCC1=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3]>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH:20]2[CH2:22][CH2:21]2)=[N:8][C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:10][C:11]=1[CH3:12])=[O:5])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 25517Ammonium ChlorideHCID 866719032-Chloro-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid ethyl esterHCID 178418630HCID 178418630, Verbindung

Produkt 1

HCID 708168332-Cyclopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid ethyl esterAusbeute 211,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5483663
Ferric acetylacetonate
Katalysator
HCID 22156051tetrahydrofuran N-methylpyrrolidinoneLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a solution 2-chloro-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid ethyl ester (7.0 g, 24.6 mmol) in tetrahydrofuran-N-methyl-2-pyrrolidone (2:3) (250 ml) is added iron(III) acetylacetonate (1.74 g, 4.92 mmol) and the mixture is cooled to −20° C. At this temperature, a solution of cyclopropylmagnesium bromide (0.7 M in tetrahydrofuran) (105 ml, 73.8 mmol) is slowly added and the mixture is warmed to 0° C. within 30 min. After completion of the reaction, 10% aqueous ammonium chloride is added and the mixture is extracted with ethyl acetate (2×). The combined organic layers are washed with water and brine, dried over magnesium sulphate and evaporated to dryness. The reaction is repeated once and the combined crude products are purified by flash chromatography (silica gel, 75% ethyl acetate/cyclohexane) to yield 2-cyclopropyl-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid ethyl ester (15.1 g).

Aufarbeitung

  1. temperaturethe mixture is warmed to 0° C. within 30 min
  2. additionis added
  3. extractionthe mixture is extracted with ethyl acetate (2×)
  4. washThe combined organic layers are washed with water and brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness
  7. customthe combined crude products are purified by flash chromatography (silica gel, 75% ethyl acetate/cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-915eb9545be342ed95a6283ba0b07327
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09168259B2

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