Isovanillin → HCID 23450397, compound

HRID 1839527Notes

Reaction equation

HRID 1839527 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[OH:11].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C:19]#[N:20])[CH:13]=1.[OH-].[Na+]>CO>[C:19](/[C:18](/[C:14]1[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=1)=[CH:7]\[C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[C:4]([OH:11])[CH:5]=1)#[N:20]

Participants

5

Reactant 3

HCID 12127IsovanillinHCID 14798Sodium HydroxideHCID 809233-Pyridineacetonitrile

Product 1

HCID 23450397HCID 23450397, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-methoxy-3-hydroxybenzaldehyde (0.5 g, 3.3 mmoles), 3-pyridylacetonitrile (0.35 ml, 3.3 mmoles) and 50% w/v of aqueous NaOH (3 ml) in methanol (10 ml) was stirred at room temperature for 30 minutes. The yellow solid that precipitated was filtered, washed with cooled methanol (1 ml), cooled CH2Cl2 (5 ml) and dried under vacuum over P2O5 to yield 0.5 g (60%) of the title compound as a yellow solid. 1H-NMR (CD3OD) 8.8 (m, 1H), 8.5 (m, 1H), 8.1 (m, 1H), 7.7 (s, 1H), 7.5 (m, 1H), 7.3 (d, 1H), 7.2 (d, 1H), 6.8 (d, 1H). Mass Spectrum m/e (M+1) 253.

Workup

  1. filtrationThe yellow solid that precipitated was filtered
  2. washwashed with cooled methanol (1 ml)
  3. temperaturecooled CH2Cl2 (5 ml)
  4. dry with materialdried under vacuum over P2O5

Sources & evidence

ORD record
ord-b18d3f37185443beb59a03ca37cb1d7e
Source dataset
uspto-grants-2004_01
Patent number
US06677383B1

Reaction notes

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