Water → 6-(4-Formyl-2-methylphenoxy)nicotinonitrile

HRID 130722

Reaction equation

HRID 130722 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:10].C([O-])([O-])=O.[K+].[K+].Cl[C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][N:19]=1.O>CN(C=O)C>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][N:19]=2)=[C:3]([CH3:10])[CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1399014-Hydroxy-3-methylbenzaldehydeHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 597302456-(4-Formyl-2-methylphenoxy)nicotinonitrileYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 4-hydroxy-3-methyl-benzaldehyde (401 mg, 2.94 mmol), K2CO3 (570 mg, 4.12 mmol) and 6-chloronicotinonitrile (408 mg, 2.94 mmol) in DMF (6 ml), heat at 100° C. After 4 h cool to ambient temperature and pour into water. Extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4 and eliminate the solvent. Dry under vacuum at 45° C. overnight to get the title compound (680 mg, 97%). 1H-NMR (CDCl3, 400 MHz): 9.99 (s, 1H), 8.43 (d, 1H, J=2.5 Hz), 7.97 (dd, 1H, J=2.5 and 8.8 Hz), 7.84 (bs, 1H), 7.80 (dd, 1H, J=2.5 and 8.8 Hz), 7.22 (d, 1H, J=8.4 Hz), 7.11 (d, 1H, J=8.4 Hz), 2.24 (s, 3H).

Workup

  1. extractionExtract the aqueous layer with EtOAc
  2. dry with materialDry the organic layer over Na2SO4
  3. customDry under vacuum at 45° C. overnight

Sources & evidence

ORD record
ord-e6711d9e40a94a29adc61f2855fa4077
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Linked notes

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