Benzaldehyde → 6,7-difluoro-3-styryl-1H-quinoxalin-2-one

HRID 584660Notes

Reaction equation

HRID 584660 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[NH:8][C:7](=[O:13])[C:6]([CH3:14])=[N:5]2.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)(=O)C.S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[NH:8][C:7](=[O:13])[C:6]([CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[N:5]2

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 3894396,7-difluoro-3-methyl-1H-quinoxalin-2-one

Product 1

HCID 541667626,7-difluoro-3-styryl-1H-quinoxalin-2-oneYield 88%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
85 °C

Procedure

6,7-Difluoro-3-methyl-1H-quinoxalin-2-one (2 g, 10.2 mmol) was dissolved in a mixture of glacial acetic acid (40 ml) and 98% sulfuric acid (4 ml). Benzaldehyde (1.08 g, 10.2 mmol) was added and the resulting mixture was stirred at reflux temperature for 3.5 hours. The mixture was allowed to cool to 85° C. and then poured onto ice (400 ml). The solid was filtered, washed with water and ethyl acetate and dried in vacuo at 30° C. overnight to afford 2.5 g (88%) of 6,7-difluoro-3-styryl-1H-quinoxalin-2-one.

Workup

  1. temperatureat reflux temperature for 3.5 hours
  2. additionpoured onto ice (400 ml)
  3. filtrationThe solid was filtered
  4. washwashed with water and ethyl acetate
  5. customdried in vacuo at 30° C. overnight

Sources & evidence

ORD record
ord-04a8a1a5ed9b42eaaa7eb001c32c3b5f
Source dataset
uspto-grants-2005_08
Patent number
US06927214B1

Reaction notes

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