Ozone → 7,8-dimethoxy-4-(4-chloro-phenyl)-5,6-dihydro-4H-1,3,4-triaza-phenalen-5-ol

HRID 1351222Notes

Reaction equation

HRID 1351222 reaction equation
[CH2:1]([C:4]1[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=[C:10]2[C:5]=1[C:6]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)=[N:7][CH:8]=[N:9]2)[CH:2]=C.[O:26]=[O+][O-]>CO>[CH3:15][O:14][C:13]1[C:12]([O:16][CH3:17])=[CH:11][C:10]2=[C:5]3[C:4]=1[CH2:1][CH:2]([OH:26])[N:18]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:6]3=[N:7][CH:8]=[N:9]2

Participants

4

Reactant 2

HCID 24823OzoneHCID 11245215(5-Allyl-6,7-dimethoxy-quinazolin-4-yl)-(4-chloro-phenyl)-amine

Product 1

HCID 210984057,8-dimethoxy-4-(4-chloro-phenyl)-5,6-dihydro-4H-1,3,4-triaza-phenalen-5-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (5-allyl-6,7-dimethoxy-quinazolin-4-yl)-(4-chloro-phenyl)-amine (0.14 g, 0.39 mmol) (from Example 16, Step E, supra), in methanol (50 mL) at −78° C. was passed a continuous stream of O3 until the color of the solution became blue. The reaction solution was then purged with argon, and methyl sulfide (5 mL) (Aldrich) was added. The reaction mixture was slowly warmed to room temperature and stirred overnight. The solution was concentrated, the residue was dried in vacuo to give the desired 7,8-dimethoxy-4-(4-chloro-phenyl)-5,6-dihydro-4H-1,3,4-triaza-phenalen-5-ol as a crude yellow solid. (Yield 0.14 g, 100%).

Workup

  1. customat −78° C.
  2. customThe reaction solution was then purged with argon, and methyl sulfide (5 mL) (Aldrich)
  3. additionwas added
  4. concentrationThe solution was concentrated
  5. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-8aa03f54c83b40b481caf34d031831cf
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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