HCID 86748042, compound → HCID 86748041, compound

HRID 1741634Notes

Reaction equation

HRID 1741634 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][C:3]=1[C:18]([O-])=[O:19]>C1(C)C=CC=CC=1>[OH:19][CH2:18][C:3]1[CH:4]=[C:5]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:7][C:2]=1[CH3:1]

Participants

3

Reactant 1

HCID 86748042HCID 86748042, compound

Product 1

HCID 86748041HCID 86748041, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 464 g 6-methyl-2,3,5-pyridinetricarboxylic acid, 2,3-diethyl ester in 2.5 L toluene is cooled, under nitrogen, 5° with mechanical stirring while 200 mL of borane-dimethylsulfide complex is added dropwise over a one hour and 30 minute period. After stirring at room temperature for three days, the reaction is cooled to 10° and quenched with 250 mL of concentrated hydrochloric acid. A further 500 mL of 3M hydrochloric acid and 250 mL of ethyl acetate is added, and the reaction is vigorously stirred for three hours and 30 minutes. The organic layer can be filter chromatographed through silica gel and concentrated in vacuo to recover 96 g unreacted starting material. The aqueous layer is neutralized with 50% sodium hydroxide, extracted with ethyl acetate, concentrated in vacuo, and chromatographed on silica gel using hexane-ethyl acetate mixtures to afford 44 g of the desired product as an oil.

Workup

  1. additionis added dropwise over a one hour and 30 minute period
  2. stirringAfter stirring at room temperature for three days
  3. temperaturethe reaction is cooled to 10°
  4. customquenched with 250 mL of concentrated hydrochloric acid
  5. additionA further 500 mL of 3M hydrochloric acid and 250 mL of ethyl acetate is added
  6. stirringthe reaction is vigorously stirred for three hours and 30 minutes
  7. filtrationThe organic layer can be filter
  8. customchromatographed through silica gel
  9. concentrationconcentrated in vacuo
  10. customto recover 96 g
  11. extractionextracted with ethyl acetate
  12. concentrationconcentrated in vacuo
  13. customchromatographed on silica gel

Sources & evidence

ORD record
ord-ace84cc6741042e59eb43c469df0567e
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

Loading…