4-Bromo-2-fluoroaniline → HCID 21701595, compound

HRID 1596264Notes

Reaction equation

HRID 1596264 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[C:22]([F:27])[CH:21]=1>C(O)(C)C>[ClH:1].[Br:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)=[C:22]([F:27])[CH:21]=1

Participants

4

Reactant 2

HCID 1230504-Bromo-2-fluoroanilineHCID 107306534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline

Product 1

HCID 21701595HCID 21701595, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline (1 07 mg, 0.4 mmol) and 4-bromo-2-fluoroaniline (76 mg, 0.4 mmol) in isopropanol (7 ml) was heated at reflux for 2 hours. The mixture was allowed to cool to ambient temperature, the precipitated solid was collected by filtration, washed with isopropanol and ether and dried to give 4-(4-bromo-2-fluoroanilino)6-methoxy-7-(2-methoxyethoxy)quinazoline hydrochloride (151 mg, 82%) as an off-white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with isopropanol and ether
  5. customdried

Sources & evidence

ORD record
ord-9404e00b84c8408b827e44b9057da70a
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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