4-Pyridinecarboxaldehyde → HCID 178519078, compound

HRID 1967949Notes

Reaction equation

HRID 1967949 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-bafd0379b0924a0e85073ac5c003862d
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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