5-Amino-2-bromo-4-fluorophenol → 4-(4-Chloro-2-fluoro-5-hydroxyanilino)-6,7-dimethoxyquinazoline hydrochloride

HRID 634657Notes

Reaction equation

HRID 634657 reaction equation
[ClH:1].[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1.Br[C:18]1[C:24]([OH:25])=[CH:23][C:21]([NH2:22])=[C:20]([F:26])[CH:19]=1>C(O)(C)C>[ClH:2].[Cl:1][C:18]1[C:24]([OH:25])=[CH:23][C:21]([NH:22][C:3]2[C:12]3[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=[CH:5][N:4]=2)=[C:20]([F:26])[CH:19]=1

Participants

4

Reactant 2

HCID 109656515-Amino-2-bromo-4-fluorophenolHCID 220221614-Chloro-6,7-dimethoxyquinazoline hydrochloride

Product 1

HCID 212602954-(4-Chloro-2-fluoro-5-hydroxyanilino)-6,7-dimethoxyquinazoline hydrochlorideYield 47%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6,7-dimethoxyquinazoline hydrochloride (2.1 g, 8 mmol), (prepared as described for the starting material in Example 1 but without the aqueous work up), and 4-chloro-2-fluoro-5-hydroxyaniline (1.43 g, 8.9 mmol), (as described in EP 61741 A2), in isopropanol (150 ml) was heated at reflux for 2 hours. The mixture was allowed to cool, the solid product collected by filtration, washed with isopropanol and dried to give 4-(4-chloro-2-fluoro-5-hydroxyanilino)-6,7-dimethoxyquinazoline hydrochloride (1.45 g, 47%).

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 2 hours
  4. temperatureto cool
  5. filtrationthe solid product collected by filtration
  6. washwashed with isopropanol
  7. customdried

Sources & evidence

ORD record
ord-a67ad28b25eb49ebaa664d261d85bee1
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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