4-Pyridinecarboxaldehyde → HCID 178519078, compound

HRID 907831Notes

Reaction equation

HRID 907831 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:11].[CH:12](=O)[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(O)C>[N:16]1[CH:17]=[CH:18][C:13](/[CH:12]=[N:1]/[C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][O:5][C:6]3=[O:11])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 24436Sodium SulfateHCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-one

Product 1

HCID 178519078HCID 178519078, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-aminoisobenzofuran-1(3H)-one (894 mg, 6 mmol), isonicotinaldehyde (2.568 g, 24 mmol) and anhydrous sodium sulfate (3.6 g) in anhydrous ethanol (70 mL) was heated to reflux for two days. The mixture was cooled to room temperature and filtered. The filtrate was concentrated to give the crude product. The crude product was washed with petroleum ether to give (E)-4-(pyridin-4-ylmethyleneamino)isobenzofuran-1(3H)-one (1.1 g, yield 77%) as a white solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 5.44 (s, 1H), 7.40-7.42 (d, J=7.6 Hz, 1H), 7.59-7.63 (t, J=7.6 Hz, 1H), 7.77-7.79 (d, J=5.6 Hz, 2H), 7.84-7.86 (d, J=7.6 Hz, 1H), 8.54 (s, 1H), 8.81-8.82 (d, J=4.8 Hz, 1H); LC-MS (ESI) m/z: 239(M+1)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for two days
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customto give the crude product
  6. washThe crude product was washed with petroleum ether

Sources & evidence

ORD record
ord-05eb75a3a182490d86ab07a9d35e7bad
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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