Ammonia → 8-Iodo-2,7-dimethylquinazolin-4(3H)-one

HRID 2092298Notes

Reaction equation

HRID 2092298 reaction equation
[NH3:1].[I:2][C:3]1[C:8]2[N:9]=[C:10]([CH3:14])[O:11][C:12](=O)[C:7]=2[CH:6]=[CH:5][C:4]=1[CH3:15]>CCOC(C)=O>[I:2][C:3]1[C:4]([CH3:15])=[CH:5][CH:6]=[C:7]2[C:8]=1[N:9]=[C:10]([CH3:14])[NH:1][C:12]2=[O:11]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 584664568-iodo-2,7-dimethyl-4H-benzo[d][1,3]oxazin-4-one

Product 1

HCID 1359656988-Iodo-2,7-dimethylquinazolin-4(3H)-oneYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Anhydrous ammonia (50 mL) was condensed in a 500 mL 3 necked flasked containing 8-iodo-2,7-dimethyl-4H-benzo[d][1,3]oxazin-4-one (8.5 g, 28 mmol) cooled to −78° C., and the reaction was stirred for 3 h. The cooling bath was removed and the solvent was allowed to evaporate at RT. 1 N Sodium hydroxide (100 mL) was added to the reaction and stirred at reflux for 1 h. The reaction was cooled down to 0° C. and acidified to pH 3 with 5 N HCl. The resulting precipitate was collected by filtration, washed with water and dried in a vacuum oven at 60° C. overnight. 8-Iodo-2,7-dimethylquinazolin-4(3H)-one (8 g, 94% yield) was obtained as a white solid. MS (M+H)+ 301.

Workup

  1. customThe cooling bath was removed
  2. customto evaporate at RT
  3. addition1 N Sodium hydroxide (100 mL) was added to the reaction
  4. stirringstirred
  5. temperatureat reflux for 1 h
  6. temperatureThe reaction was cooled down to 0° C.
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed with water
  9. customdried in a vacuum oven at 60° C. overnight

Sources & evidence

ORD record
ord-2db522c8451844daa19ae04b3c6e3deb
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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