Ammonium Hydroxide → 7-Methoxy-4-phenylamino-quinazolin-6-ol

HRID 1351190Notes

Reaction equation

HRID 1351190 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][N:9]=[C:8]2[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)C.[NH4+].[OH-]>CO>[CH3:16][O:15][C:14]1[CH:13]=[C:12]2[C:7]([C:8]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:9][CH:10]=[N:11]2)=[CH:6][C:5]=1[OH:4]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 210983996-Acetoxy-7-methoxy-4-phenylamino-quinazoline

Product 1

HCID 210984067-Methoxy-4-phenylamino-quinazolin-6-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-acetoxy-7-methoxy-4-phenylamino-quinazoline (1.01 g, 3.27 mmol) (from Example 15, Step A, supra) in MeOH (30 mL) was added an aqueous solution of NH4OH (29%, 2.0 g, 31.4 mmol). The reaction mixture was stirred at room temperature for 18 hours, and then heated at 100° C. for 1.5 hours. The mixture was then cooled to room temperature and filtered. The precipitate was collected and dried in vacuo to give the desired 7-methoxy-4-phenylamino-quinazolin-6-ol as a white solid. (Yield 0.6 g, 69%).

Workup

  1. temperatureheated at 100° C. for 1.5 hours
  2. temperatureThe mixture was then cooled to room temperature
  3. filtrationfiltered
  4. customThe precipitate was collected
  5. customdried in vacuo

Sources & evidence

ORD record
ord-33cfa0c82ec64d1684b7940ff6ce47c1
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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