Water → Afloqualone

HRID 1658726Notes

Reaction equation

HRID 1658726 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.O.C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>CO.Cl>[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

7

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 637924(3H)-Quinazolinone, 2-(fluoromethyl)-3-(2-methylphenyl)-6-nitro-HCID 516892Sodium Bicarbonate

Product 1

HCID 2040AfloqualoneYield 84%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

2.5 g of 2-fluoromethyl-3-(o-tolyl)-6-nitro-4(3H)-quinazolinone are suspended in 40 ml of methanol, and a solution of 6.0 g of stannous chloride in 6.0 ml of concentrated hydrochloric acid is added dropwise thereto at 5° to 10°C for 15 minutes. The mixture is stirred at the same temperature for 15 minutes and then at room temperature for 2.5 hours. After the reaction, the mixture becomes a clear solution. The solution thus obtained is decolorized with 0.25 g of activated carbon. 200 ml of water and 100 ml of chloroform are added to the solution. Then, the solution is neutralized with sodium bicarbonate, stirred and filtered to remove insoluble materials. The chloroform layer is separated, dried and then concentrated to dryness. The residue thus obtained is crystallized with 15 ml of isopropanol, and the crystalline precipitate is collected by filtration. 1.9 g of 2-fluoromethyl-3-(o-tolyl)-6-amino-4(3H)-quinazolinone are obtained.

Workup

  1. waitat room temperature for 2.5 hours
  2. customAfter the reaction
  3. customThe solution thus obtained
  4. stirringstirred
  5. filtrationfiltered
  6. customto remove insoluble materials
  7. customThe chloroform layer is separated
  8. customdried
  9. concentrationconcentrated to dryness
  10. customThe residue thus obtained
  11. customis crystallized with 15 ml of isopropanol
  12. filtrationthe crystalline precipitate is collected by filtration

Sources & evidence

ORD record
ord-220c9c96433f4278b713e93d7e0e93c6
Source dataset
uspto-grants-1976_06
Patent number
US03966731

Reaction notes

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