Dimethylformamide → 6-[(5-Chloro-2-hydroxyphenyl)methyl]-2-pyridinecarboxylic acid

HRID 2356636

Reaktionsgleichung

Reaktionsgleichung von HRID 2356636
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20]CC2C=CC(Cl)=CC=2F)=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([O:17]CC)=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1.C[S-].[Na+].CN(C)C=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH:7]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 4378561Sodium methanethiolateHCID 59384237Ethyl 6-(5-chloro-2-((4-chloro-2-fluorobenzyl)oxy)benzyl)picolinate

Produkt 1

HCID 684564716-[(5-Chloro-2-hydroxyphenyl)methyl]-2-pyridinecarboxylic acidAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of ethyl 6-[(5-chloro-2-{[(4-chloro-2-fluorophenyl)methyl]oxy}-phenyl)methyl]-2-pyridinecarboxylate (453 mg), sodium thiomethoxide (370 mg) and dimethylformamide (5 ml) was stirred at 100° C. for 2.5 hours. After cooling water (30 ml) was added and the mixture extracted with ethyl acetate (2×25 ml). The aqueous layer was acidified with conc. hydrochloric acid and extracted with ethyl acetate (2×25 ml). The combined extracts were washed with water (10 ml), dried (MgSO4) and concentrated in vacuo. The residue was washed with water and recrystallised from ether to afford the title compound (208 mg, 76%) as a pale buff solid.

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture extracted with ethyl acetate (2×25 ml)
  3. extractionextracted with ethyl acetate (2×25 ml)
  4. washThe combined extracts were washed with water (10 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with water
  8. customrecrystallised from ether

Quellen und Nachweise

ORD-Eintrag
ord-4d24b44417134b4da603490b1d99dbfc
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07759369B2

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