Ammonium Hydroxide → 4-[(3-Chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-ol

HRID 1351208Notes

Reaction equation

HRID 1351208 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][C:21]([F:24])=[C:20]([Cl:25])[CH:19]=1)(=O)C.[NH4+].[OH-]>CO>[Cl:25][C:20]1[CH:19]=[C:18]([NH:17][C:8]2[C:7]3[C:12](=[CH:13][C:14]([O:15][CH3:16])=[C:5]([OH:4])[CH:6]=3)[N:11]=[CH:10][N:9]=2)[CH:23]=[CH:22][C:21]=1[F:24]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 210983964-((3-Chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl acetate

Product 1

HCID 104712174-[(3-Chloro-4-fluorophenyl)amino]-7-methoxyquinazolin-6-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-acetoxy-4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinazoline (1.54 g, 4.26 mmol) (from Example 18, Step A, supra) in MeOH (30 mL) was added an aqueous solution of NH4OH (29%, 0.86 mL, 12.7 mmol). The reaction mixture was stirred at room temperature for 18 hours, 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 4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinazolin-6-ol as a gray solid. (Yield 1.21 g, 89%).

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-b062f12dd8e6481ab3d0220570ce2dfb
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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