Sulfuric Acid → HCID 54326466, compound

HRID 584656Notes

Reaction equation

HRID 584656 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[C:6]([CH3:14])=[N:5]2.S(=O)(=O)(O)O.[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[C:6]([CH:14]=[CH:25][C:24]1[CH:27]=[CH:28][C:21]([F:20])=[CH:22][CH:23]=1)=[N:5]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 680234-FluorobenzaldehydeHCID 1106421273148-15-9

Product 1

HCID 54326466HCID 54326466, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Conditions

Temperature
85 °C

Procedure

6,7-Dichloro-3-methyl-1H-quinoxalin-2-one (5 g, 22 mmol) (prepared as described in: Collins, J. L.; Dambek, P. J.; Goldstein, S. W.; Faraci, W. S. Bioorg. Med. Chem. Lett. 1992, 2, 915-8) was dissolved in a mixture of glacial acetic add (100 ml) and 98% sulfuric acid (10 ml). 4-Fluorobenzaldehyde (2.3 ml, 22 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 (500 ml). The solid was filtered, washed with water and ethyl acetate and dried in vacuo at 30° C. overnight to afford 7.2 g (99%) of 6,7-dichloro-3-[2-(4-fluorophenyl)vinyl]-1H-quinoxalin-2-one.

Workup

  1. temperatureat reflux temperature for 3.5 hours
  2. additionpoured onto ice (500 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-6db8a7d819374d089def69b00983b472
Source dataset
uspto-grants-2005_08
Patent number
US06927214B1

Reaction notes

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