Ammonium Hydroxide → 4-(3-Bromoanilino)-6-hydroxy-7-methoxyquinazoline

HRID 1351203Notes

Reaction equation

HRID 1351203 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]=[C:20]([Br:24])[CH:19]=1)(=O)C.[NH4+].[OH-]>CO>[Br:24][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][CH:21]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 187629014-[(3-Bromophenyl)amino]-6-methylcarbonyloxy-7-methoxyquinazoline

Product 1

HCID 103829564-(3-Bromoanilino)-6-hydroxy-7-methoxyquinazoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-acetoxy-4-(3-bromo-phenylamino)-7-methoxy-quinazoline (1.59 g, 4.11 mmol) (from Example 17, Step A, supra) in MeOH (30 mL) was added an aqueous solution of NH4OH (29%, 0.83 mL, 12.3 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-bromo-phenylamino)-7-methoxy-quinazolin-6-ol as a gray solid. (Yield 1.25 g, 88%).

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-ef26d7f00e544f4d81c0f8212a832185
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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