HCID 13376462, compound → HCID 13376463, compound

HRID 986649Notes

Reaction equation

HRID 986649 reaction equation
[F:1][CH2:2][C:3]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=2[CH3:20])[C:11](=[O:21])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:22]([O-])=O)[CH:9]=2)[N:4]=1>CO.Cl>[F:1][CH2:2][C:3]1[N:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=2[CH3:20])[C:11](=[O:21])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH2:22])[CH:9]=2)[N:4]=1

Participants

4

Reactant 1

HCID 13376462HCID 13376462, compound

Product 1

HCID 13376463HCID 13376463, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

2.0 g of 2-fluoromethyl-3-(2,4-dimethylphenyl)-6-nitro-4(3H)-quinazolinone are suspended in 35 ml of methanol, and a solution of 5.4 g of stannous chloride dihydrate in 5 ml of conc. hydrochloric acid is added dropwise thereto under ice-cooling and stirring. Then, the mixture is stirred at room temperature overnight. The mixture is concentrated under reduced pressure to remove methanol, and water is added to the residue. The aqueous mixture is neutralized with sodium bicarbonate, and chloroform is added thereto. After stirring the mixture, insoluble materials are filtered off. The chloroform solution is separated from the filtrate and concentrated under reduced pressure to give a crystalline residue. The thus-obtained crystals (1.4 g) are recrystallized from isopropanol. 1.2 g of 2-fluoromethyl-3-(2,4-dimethylphenyl)-6-amino-4(3H)-quinazolinone are obtained as pale yellow prisms.

Workup

  1. temperatureunder ice-cooling
  2. stirringThen, the mixture is stirred at room temperature overnight
  3. concentrationThe mixture is concentrated under reduced pressure
  4. customto remove methanol, and water
  5. additionis added to the residue
  6. additionis added
  7. stirringAfter stirring the mixture, insoluble materials
  8. filtrationare filtered off
  9. customThe chloroform solution is separated from the filtrate
  10. concentrationconcentrated under reduced pressure
  11. customto give a crystalline residue
  12. customThe thus-obtained crystals (1.4 g) are recrystallized from isopropanol

Sources & evidence

ORD record
ord-566e4a41ac0449f1b6c34a50087623c3
Source dataset
uspto-grants-1987_12
Patent number
US04714702

Reaction notes

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