Anthranilamide → 2-(2-methoxyphenyl)-3H-quinazolin-4-one

HRID 2062145Notes

Reaction equation

HRID 2062145 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(=O)([O-])[O-].[K+].[K+].[C:17](Cl)(=O)[C:18]1[C:19]([O:24][CH3:25])=[CH:20][CH:21]=[CH:22][CH:23]=1>CCOCC>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:17]1[NH:10][C:1](=[O:9])[C:2]2[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:4]=1

Participants

5

Reactant 3

HCID 6942AnthranilamideHCID 11430Potassium CarbonateHCID 889692-Methoxybenzoyl chloride

Product 1

HCID 1354360052-(2-methoxyphenyl)-3H-quinazolin-4-oneYield 73%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a 2 L three-necked round-bottomed flask equipped with an overhead stirrer and reflux condenser, anthranilamide (20.0 g, 147 mmol) and potassium carbonate (28.4 g, 206 mmol) were suspended in 1 L dry ether and heated to reflux. o-Anisoyl chloride (32.5 g, 191 mmol) was added slowly to the refluxing mixture. After 3 hours at reflux, the reaction mixture was allowed to cool to room temperature, the ether was removed under reduced pressure, and the resulting residue was filtered and washed with water. The resulting solid was then suspended in 600 mL of 5% aq. NaOH solution and boiled for one hour. The reaction was allowed to cool to room temperature, and it was neutralized with acetic acid, upon which 2-(2-methoxyphenyl)quinazolin-4(3H)-one was precipitated. The product was collected by filtration, washed with water, and dried overnight in vacuo to yield 27 g (73%) of pure 2-(2-methoxyphenyl)quinazolin-4(3H)-one. LC/MS: m/z 253.0 (M+H)+ at 3.22 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)). 1H NMR (DMSO) δ 3.86 (s, 3H), δ 7.09 (t, 1H), δ 7.18 (d, 1H), δ 7.53 (m, 2H), δ 7.70 (m, 2H), δ 7.80 (m, 1H), δ 8.14 (d, 1H), δ 12.11 (s, 1H); 13C NMR (DMSO) δ 55.75, δ 111.86, δ 120.89, δ 120.97, δ 122.74, δ 125.75, δ 126.45, δ 127.26, 8 130.41, δ 132.13, δ 134.32, δ 148.97, δ 152.48, δ 157.12, δ 161.35

Workup

  1. customIn a 2 L three-necked round-bottomed flask equipped with an overhead stirrer
  2. temperaturereflux condenser
  3. temperatureheated to reflux
  4. temperatureAfter 3 hours at reflux
  5. customthe ether was removed under reduced pressure
  6. filtrationthe resulting residue was filtered
  7. washwashed with water
  8. temperatureto cool to room temperature
  9. customwas precipitated
  10. filtrationThe product was collected by filtration
  11. washwashed with water
  12. customdried overnight in vacuo

Sources & evidence

ORD record
ord-a18c337b8ac8419ea7cae5225890ea13
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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