Hydrochloric Acid → Afloqualone

HRID 1658725Notes

Reaction equation

HRID 1658725 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.Cl>[H][H].[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

5

Reactant 2

HCID 313Hydrochloric AcidHCID 637924(3H)-Quinazolinone, 2-(fluoromethyl)-3-(2-methylphenyl)-6-nitro-

Product 1

HCID 2040AfloqualoneYield 72%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 178418361HCID 178418361, compoundSolvent2×

Procedure

A mixture of 2.0 g of 2-fluoromethyl-3-(o-tolyl)-6-nitro-4(3H)-quinazolinone, 0.2 g of 5 % palladium-carbon and 100 ml of 10 % hydrochloric acid is shaken at 40°C for 1.5 hours in hydrogen gas. The initial pressure of hydrogen gas is adjusted to 48 lb. After said reaction, the mixture is cooled and filtered to remove the catalyst. The filtrate is neutralized with sodium bicarbonate, and the precipitate is extracted with benzene. The benzene solution is dried and then evaporated to remove solvent. The residue thus obtained is recrystallized from isopropanol. 1.3 g of 2-fluoromethyl-3-(o-tolyl)-6-amino-4(3H)-quinazolinone are obtained.

Workup

  1. customreaction
  2. temperaturethe mixture is cooled
  3. filtrationfiltered
  4. customto remove the catalyst
  5. extractionthe precipitate is extracted with benzene
  6. dry with materialThe benzene solution is dried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue thus obtained
  10. customis recrystallized from isopropanol

Sources & evidence

ORD record
ord-5d7ba91644ee47b887129ba589b30b14
Source dataset
uspto-grants-1976_06
Patent number
US03966731

Reaction notes

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