Acetic Anhydride → 4(3H)-Quinazolinone, 2-(fluoromethyl)-3-(2-methylphenyl)-6-nitro-

HRID 1658723Notes

Reaction equation

HRID 1658723 reaction equation
[F:1][CH2:2][C:3]([NH:5][C:6]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:7]=1[C:8]([NH:10][C:11]1[C:12]([CH3:17])=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:9])=O.C(OC(=O)C)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[F:1][CH2:2][C:3]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[C:8](=[O:9])[C:7]2[C:6](=[CH:21][CH:20]=[C:19]([N+:22]([O-:24])=[O:23])[CH:18]=2)[N:5]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 215254582-(2-Fluoroacetamido)-N-(2-methylphenyl)-5-nitrobenzamide

Product 1

HCID 637924(3H)-Quinazolinone, 2-(fluoromethyl)-3-(2-methylphenyl)-6-nitro-Yield 99%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

16.5 g(0.05 mol) of N-(2-fluoroacetamido-5-nitrobenzoyl)-o-toluidine and 25.5 g(0.25 mol) of acetic acid anhydride are dissolved in 250 ml of glacial acetic acid. The solution is refluxed for 2 hours under heating. Then, the reaction solution is evaporated to remove solvent. The residue thus obtained is poured into ice-water, and the aqueous mixture is adjusted to pH 9 with potassium carbonate. The crystalline precipitate is collected by filtration. 15.5 g of 2-fluoromethyl-3-(o-tolyl)-6-nitro-4(3H)-quinazolinone are obtained.

Workup

  1. temperatureThe solution is refluxed for 2 hours
  2. temperatureunder heating
  3. customThen, the reaction solution is evaporated
  4. customto remove solvent
  5. customThe residue thus obtained
  6. filtrationThe crystalline precipitate is collected by filtration

Sources & evidence

ORD record
ord-9ce0482766ac427bbb27024f7829917a
Source dataset
uspto-grants-1976_06
Patent number
US03966731

Reaction notes

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