Vanillin → HCID 47150217, compound

HRID 130849Notes

Reaction equation

HRID 130849 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.Cl[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][N:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:2]([C:3]1[CH:11]=[CH:10][C:8]([O:9][C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][N:14]=2)=[C:5]([O:6][CH3:7])[CH:4]=1)=[O:1]

Participants

5

Reactant 3

HCID 1183VanillinHCID 11430Potassium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 47150217HCID 47150217, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Take up vanillin (1.0 g, 6.57 mmol), 6-chloronicotinonitrile (0.911 g, 6.57 mmol) and K2CO3 (1.36 g, 9.86 mmol) in DMF (16.4 mL). Stir at room temperature overnight, then heat at 100° C. for 3 hours. Cool the reaction mixture to room temperature before quenching with water (75 mL). Extract with dichloromethane (2×150 mL). Wash the organic layer with brine (1×75 mL), dry over MgSO4, filter and concentrate to give the title compound (1.65 g, 98.8%): TOF MS ES+ 255.1 (M+H)+, HRMS calcd for C14H11N2O3 255.0770 (M+H)+, found 255.0776, time 0.38 min; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 20-99% over 23 min], tR=12.2 min, 100% purity.

Workup

  1. temperatureheat at 100° C. for 3 hours
  2. temperatureCool the reaction mixture to room temperature
  3. custombefore quenching with water (75 mL)
  4. extractionExtract with dichloromethane (2×150 mL)
  5. washWash the organic layer with brine (1×75 mL)
  6. dry with materialdry over MgSO4
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-e20365f4b9274b48bf30bac76feec265
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

Loading…