4-Hydroxybenzaldehyde → HCID 9837407, compound

HRID 1839528Notes

Reaction equation

HRID 1839528 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][C:17]#[N:18])[CH:11]=1.[OH-].[Na+]>CO>[C:17](/[C:16](/[C:12]1[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=1)=[CH:6]\[C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1)#[N:18]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 14798Sodium HydroxideHCID 809233-Pyridineacetonitrile

Product 1

HCID 9837407HCID 9837407, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-hydroxybenzaldehyde (0.5 g, 4.1 mmoles), 3-pyridylacetonitrile (0.54 ml, 4.1 mmoles) and 50% w/v of aqueous NaOH (3.3 ml) in methanol (10 ml) was stirred at room temperature for 30 minutes. The yellow precipitate that formed was filtered, washed with cooled methanol (1 ml), cooled CH2Cl2 (10 ml), and dried under vacuum over P2O5 to yield 0.6 g (66%) of the title compound. 1H-NMR (CD3OD) 8.8 (d, 1H), 8.4 (m, 1H), 8.05 (m, 1H), 7.8 (m, 2H), 7.6 (s, 1H), 7.4 (m, 1H), 6.6 (m, 2H). 13C-NMR (DMSO) 177.52, 175.57, 146.59, 145.06, 144.78, 133.15, 132.73, 130.97, 123.8, 120.8, 120.3, 114.3, 88.5; Mass Spectrum m/e (M+1) 223.

Workup

  1. customThe yellow precipitate that formed
  2. filtrationwas filtered
  3. washwashed with cooled methanol (1 ml)
  4. temperaturecooled CH2Cl2 (10 ml)
  5. dry with materialdried under vacuum over P2O5

Sources & evidence

ORD record
ord-e9a18e9930354cd18e8cd441ff4d9109
Source dataset
uspto-grants-2004_01
Patent number
US06677383B1

Reaction notes

Loading…