Acetic Acid → Afloqualone

HRID 1658724Notes

Reaction equation

HRID 1658724 reaction equation
[F:1][CH2:2][C:3]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[C:11](=[O:20])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:21]([O-])=O)[CH:9]=2)[N:4]=1.C(O)(=O)C>[H][H].C(Cl)(Cl)Cl.[C].[Pd]>[F:1][CH2:2][C:3]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[C:11](=[O:20])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:21])[CH:9]=2)[N:4]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 637924(3H)-Quinazolinone, 2-(fluoromethyl)-3-(2-methylphenyl)-6-nitro-

Product 1

HCID 2040AfloqualoneYield 52.5%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 6212ChloroformSolvent2×HCID 178418361HCID 178418361, compoundSolvent3×

Procedure

A mixture of 2.0 g(0.064 mol) of 2-fluoromethyl-3-(o-tolyl)-6-nitro-4(3H)-quinazolinone, 0.2 g of 5 % palladium-carbon and 100 ml of acetic acid is shaken for 30 minutes in hydrogen gas. The initial pressure of hydrogen gas is adjusted to 46 lb and the mixture is heated with an infrared lamp during the reaction. After 30 minutes of said reaction, the pressure of hydrogen gas decreases to 6 lb. After the mixture is cooled, said mixture is filtered to remove the catalyst. The filtrate is evaporated to remove acetic acid, and the residue is dissolved in chloroform. The chloroform solution is washed with 5 % aqueous sodium hydroxide and water, successively. Then, the solution is dried and evaporated to remove solvent. The oily residue thus obtained is dissolved in 2 ml of chloroform, and the chloroform solution is passed through a column of 200 g of silica gel. The silical gel column is eluted with ethyl acetate-benzene(1 : 1). Then, the eluate is evaporated to remove solvent. The crude crystal obtained is washed with isopropylether and recrystallized from isopropanol. 0.95 g of 2-fluoromethyl-3-(o-tolyl)-6-amino-4(3H)-quinazolinone is obtained.

Workup

  1. temperaturethe mixture is heated with an infrared lamp during the reaction
  2. customAfter 30 minutes of said reaction
  3. temperatureAfter the mixture is cooled
  4. filtrationis filtered
  5. customto remove the catalyst
  6. customThe filtrate is evaporated
  7. customto remove acetic acid
  8. dissolutionthe residue is dissolved in chloroform
  9. washThe chloroform solution is washed with 5 % aqueous sodium hydroxide and water
  10. customThen, the solution is dried
  11. customevaporated
  12. customto remove solvent
  13. customThe oily residue thus obtained
  14. washThe silical gel column is eluted with ethyl acetate-benzene(1 : 1)
  15. customThen, the eluate is evaporated
  16. customto remove solvent
  17. customThe crude crystal obtained
  18. washis washed with isopropylether
  19. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-1fbb47a2e5064ac2801a19407e40baa7
Source dataset
uspto-grants-1976_06
Patent number
US03966731

Reaction notes

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