Methanol → HCID 52983911, compound

HRID 2272004Notes

Reaction equation

HRID 2272004 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]#N)=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.[OH-:17].[Na+].C[OH:20]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]([OH:20])=[O:17])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 14798Sodium HydroxideHCID 671926753-(3-Methoxyphenyl)pyridine-2-carbonitrile

Product 1

HCID 52983911HCID 52983911, compound

Procedure

A mixture of 3-(3-methoxyphenyl)-pyridine-2-carbonitrile (12.00 g), 15 M aqueous NaOH solution (40 mL), and methanol (60 mL) is stirred at reflux temperature for 7 h. After cooling to room temperature, most of the methanol is evaporated and the residue is cooled in an ice bath and adjusted to pH value ca. 4-5 by the careful addition of concentrated hydrochloric acid. The resulting mixture is concentrated to ca. 50 ml by evaporation and extracted with dichloromethane/methanol (9:1) several times. The aqueous phase is then adjusted to pH value 2-3 using concentrated hydrochloric acid and extracted again with dichloromethane/methanol (9:1). The combined extracts are dried (Na2SO4) and the solvent is evaporated to give the title compound as a foam-like solid. Yield: 11.88 g (91% of theory); LC (method 1): tR=1.70 min; Mass spectrum (ESI+): m/z=230 [M+H]+.

Workup

  1. temperatureat reflux temperature for 7 h
  2. customis evaporated
  3. temperaturethe residue is cooled in an ice bath
  4. additionadjusted to pH value ca. 4-5 by the careful addition of concentrated hydrochloric acid
  5. concentrationThe resulting mixture is concentrated to ca. 50 ml by evaporation
  6. extractionextracted with dichloromethane/methanol (9:1) several times
  7. extractionextracted again with dichloromethane/methanol (9:1)
  8. dry with materialThe combined extracts are dried (Na2SO4)
  9. customthe solvent is evaporated

Sources & evidence

ORD record
ord-231f6ceb003f4b9f9bdd557edcdab012
Source dataset
uspto-grants-2015_09
Patent number
US09120769B2

Reaction notes

Loading…