4-Hydroxybenzaldehyde → 6-(4-Formylphenoxy)nicotinonitrile

HRID 1177979Notes

Reaction equation

HRID 1177979 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=1.[OH:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1>CN(C=O)C.O>[CH:21]([C:20]1[CH:23]=[CH:24][C:17]([O:16][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][N:9]=2)=[CH:18][CH:19]=1)=[O:22]

Participants

6

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 471502166-(4-Formylphenoxy)nicotinonitrileYield 84.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

K2CO3 (450 mg, 3.27 mmol) and 6-chloronicotinonitrile (270 mg, 1.97 mmol) were added to 4-hydroxy-benzaldehyde (200 mg, 1.64 mmol) in DMF (2 mL) and the resulting mixture was heated to 70° C. for 3 hrs. The reaction mixture was then diluted with water and the resulting was filtered and dried to afford 310 mg (79.1% yield) of 6-(4-formyl-phenoxy)nicotinonitrile. LCMS Purity: 97.3%.

Workup

  1. filtrationthe resulting was filtered
  2. customdried

Sources & evidence

ORD record
ord-b69b6ca2d177493ab0893f30a84bef48
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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