Water → 2-Chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester

HRID 922054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 922054
[CH3:1][O:2][C:3]([C:5]1[C:6]([Cl:13])=[N:7][C:8](Cl)=[CH:9][C:10]=1[CH3:11])=[O:4].C([O-])([O-])=O.[K+].[K+].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:6]([Cl:13])=[N:7][C:8]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:9][C:10]=1[CH3:11])=[O:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 46911843Methyl 2,6-dichloro-4-methylnicotinate

Produkt 1

HCID 866643312-Chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylesterAusbeute 30,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5.2 g (23.7 mmol) 2,6-dichloro-4-methyl-pyridine-3-carboxylic acid methylester, 3.94 g (28.5 mmol) K2CO3 and 2.06 ml (23.7 mmol) morpholine in DMF (48 ml) was heated to 60° C. for 16 h. Then the mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 4:1) provided 1.95 g (7.2 mmol, 30%) 2-chloro-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by CC (hexane/EtOAc 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-36631b82bbdf4f789c547b7dd4849c31
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278103B2

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