Methanol → Methyl 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinate

HRID 1424663

Reaktionsgleichung

Reaktionsgleichung von HRID 1424663
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])[N:5]=[C:4]([C:19]([O:21][CH2:22]C2C=CC=CC=2)=[O:20])[CH:3]=1.CO.C[O-].[Na+]>O>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[CH:3]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 70495788Benzyl 4-amino-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinate

Produkt 1

HCID 70495727Methyl 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Benzyl 4-amino-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)picolinate (3.00 g, 7.41 mmol) was added to CH3OH (35 mL). Sodium methoxide (25 wt % in CH3OH; 2.0 mL, 8.9 mmol) was added to the reaction mixture and allowed to stir for 24 h. Water (50 mL) was added to the reaction mixture and the mixture was concentrated under reduced pressure to remove most of the CH3OH. The mixture was extracted with EtOAc (2×40 mL), and the combined organic layers were washed with water (40 mL) and satd sodium chloride (40 mL) and concentrated under reduced pressure to provide methyl 4-amino-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinate as a pale yellow solid (1.86 g; 67% purity by LC area).

Aufarbeitung

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto remove most of the CH3OH
  3. extractionThe mixture was extracted with EtOAc (2×40 mL)
  4. washthe combined organic layers were washed with water (40 mL) and satd sodium chloride (40 mL)
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-09d72e8b9f3a4f0abb4c941210a3856d
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927731B2

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