Sodium Hydroxide → HCID 10220324, compound

HRID 1839526Notes

Reaction equation

HRID 1839526 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][C:18]#[N:19])[CH:12]=1.[OH-].[Na+]>CO>[C:18](/[C:17](/[C:13]1[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=1)=[CH:7]\[C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)#[N:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312444-MethoxybenzaldehydeHCID 809233-Pyridineacetonitrile

Product 1

HCID 10220324HCID 10220324, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred mixture of 4-methoxybenzaldehyde (2 g, 14.69 mmol) and 3-pyridylacetonitrile (1.58 ml, 14.84 mmol) in methanol (30 ml) was added 50% w/v sodium hydroxide (1 ml). The reaction was stirred for 3 hours. The reaction mixture was quenched with water (20 ml), acidified with 2N HCl, then rebasified with dilute NaOH (aq), and the reaction product was extracted successively into dichloromethene (3×20 ml). The organic solutions were dried over anhydrous MgSO4 and the solvent removed. Purification by column chromatography (SiO2, Hexane/Ethylacetate 8:2; 1:1) gave 2.01 g (58% yield) of the title compound as a straw coloured solid: 1H-NMR (CDCl3) 8.80 (d, 1H), 8.50 (m, 1H), 7.80 (m, 3H), 7.45 (s, 1H), 7.25 (m, 1H), 6.90 (m, 2H), 3.80 (s, 3H). 13C NMR (CDCl3) 161.9, 157.6, 157.5, 149.5, 146.9, 143.3, 133.1, 131.4, 130.9, 126, 123.5, 117.7, 114.5, 105.2, 55.4. Mass Spectrum m/e (M+1) 237.

Workup

  1. additionwas added 50%
  2. customThe reaction mixture was quenched with water (20 ml)
  3. extractionthe reaction product was extracted successively into dichloromethene (3×20 ml)
  4. dry with materialThe organic solutions were dried over anhydrous MgSO4
  5. customthe solvent removed
  6. customPurification by column chromatography (SiO2, Hexane/Ethylacetate 8:2; 1:1)

Sources & evidence

ORD record
ord-6c51402e82264d5397ce63867aec6f48
Source dataset
uspto-grants-2004_01
Patent number
US06677383B1

Reaction notes

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