Toluene → 4H,5H-furo(3,2-c)pyridin-4-one

HRID 734303Notes

Reaction equation

HRID 734303 reaction equation
O1C=CC=C1C=C[C:8]([N:10]=[N+]=[N-])=[O:9].[CH3:13][CH2:14][O:15][CH2:16][CH3:17].[C:18]1(C)C=CC=C[CH:19]=1>>[O:15]1[C:16]2[CH:19]=[CH:18][NH:10][C:8](=[O:9])[C:17]=2[CH:13]=[CH:14]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 3283Diethyl EtherHCID 27775243-(Furan-2-yl)-acryloyl azide

Product 1

HCID 2887464H,5H-furo(3,2-c)pyridin-4-one

Conditions

Temperature
170 °C

Procedure

3-(Furan-2-yl)-acryloyl azide (12.6 g) was dissolved in 100 ml of toluene and the resultant solution was heated up to 120° C. and stirred for 30 min. After evaporation of solvent, o-dichlorobenzene (100 ml) and a few flakes of iodine were added and resultant reaction mixture was heated up to 170° C. and stirred for 2 hours. The mixture was cooled down to ambient temperature and to this was added Et2O (100 ml). The undissolved matter was filtered off and the filtrate was poured into a mixture of Et2O (100 ml), 1N NaOH (100 ml) and water (100 ml). The corresponding aqueous layer was collected, which was acidified by 2N HCl and extracted with ethyl acetate. The organic layer was separated and dried over Na2SO4, filtered and concentrated in vacuo. The residue was precipitated from Et2O, which was collected and dried under the reduced pressure to give 5H-furo[3,2-c]pyridin-4-one (6.7 g) 1H NMR (400 MHz, DMSO-d6) ppm 11.44 (brs, 1H), 7.87 (d, J=2.3 Hz, 1H), 7.29 (d, J=7.1 Hz, 1H), 6.93 (dd, J=2.1, 0.9 Hz, 1H), 6.66 (dd, J=0.8, 7.1 Hz, 1H).

Workup

  1. customAfter evaporation of solvent, o-dichlorobenzene (100 ml)
  2. additiona few flakes of iodine were added
  3. customresultant reaction mixture
  4. stirringstirred for 2 hours
  5. temperatureThe mixture was cooled down to ambient temperature
  6. filtrationThe undissolved matter was filtered off
  7. additionthe filtrate was poured into a mixture of Et2O (100 ml), 1N NaOH (100 ml) and water (100 ml)
  8. customThe corresponding aqueous layer was collected
  9. extractionextracted with ethyl acetate
  10. customThe organic layer was separated
  11. dry with materialdried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customThe residue was precipitated from Et2O, which
  15. customwas collected
  16. customdried under the reduced pressure

Sources & evidence

ORD record
ord-a2fbb8d8fc0442d6a24c4321012d3eb5
Source dataset
uspto-grants-2009_09
Patent number
US07592352B2

Reaction notes

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