Magnesium Bromide → 4-[(3-Chloro-2-fluorophenyl)amino]-7-hydroxyquinazoline-6-carbaldehyde

HRID 1867731Notes

Reaction equation

HRID 1867731 reaction equation
[Br-].[Mg+2].[Br-].[Cl:4][C:5]1[C:6]([F:26])=[C:7]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([O:24]C)=[C:19]([CH:22]=[O:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1>N1C=CC=CC=1.O>[Cl:4][C:5]1[C:6]([F:26])=[C:7]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([OH:24])=[C:19]([CH:22]=[O:23])[CH:20]=3)[N:15]=[CH:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 82241Magnesium BromideHCID 115734924-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde

Product 1

HCID 1363684114-[(3-Chloro-2-fluorophenyl)amino]-7-hydroxyquinazoline-6-carbaldehydeYield 100.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

Solid anhydrous magnesium bromide (3.66 g, 19.9 mmol) was carefully added to a stirred solution of 4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazoline-6-carbaldehyde (2.0 g, 6.04 mmol) in pyridine (30 ml) at room temperature. The resulting suspension was heated at 130° C. for 16 hours, cooled to room temperature and concentrated to dryness to give a yellow solid. This was suspended in water (100 ml), collected by filtration and washed several times with water. The resulting yellow solid was dried to a constant weight in a vacuum oven at 40° C. to give 4-[(3-chloro-2-fluorophenyl)amino]-7-hydroxyquinazoline-6-carbaldehyde, (1.93 g, 100%); Mass Spectrum: (M+H)+ 318.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated to dryness
  3. customto give a yellow solid
  4. filtrationcollected by filtration
  5. washwashed several times with water
  6. customThe resulting yellow solid was dried to a constant weight in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-7b91894a25284a28a3c94f01ea21d098
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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