4-Chloro-2-fluoroaniline → HCID 5329015, compound

HRID 1596236Notes

Reaction equation

HRID 1596236 reaction equation
Cl.Cl[C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:10][CH:11]=2)[N:6]=[CH:5][N:4]=1.[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[C:21]([F:26])[CH:20]=1>C(O)(C)C>[Cl:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:3]2[C:12]3[C:7](=[CH:8][C:9]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:10][CH:11]=3)[N:6]=[CH:5][N:4]=2)=[C:21]([F:26])[CH:20]=1

Participants

4

Reactant 2

HCID 938984-Chloro-2-fluoroanilineHCID 21701573HCID 21701573, compound

Product 1

HCID 5329015HCID 5329015, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 4-chloro-7-(2-methoxyethoxy)quinazoline hydrochloride (624 mg, 2.27 mmol) and 4-chloro-2-fluoroaniline (305 μl, 2.6 mmol) in isopropanol (20 ml) was heated at reflux for 30 minutes. The solvent was removed by evaporation and the residue partitioned between ethyl acetate and water. The organic layer was separated, washed with aqueous sodium hydrogen carbonate solution, then with water, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with ether to give 4-(4-chloro-2-fluoroanilino)-7-(2-methoxyethoxy)quinazoline (662 mg, 84%) as a white solid.

Workup

  1. temperatureat reflux for 30 minutes
  2. customThe solvent was removed by evaporation
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. washwashed with aqueous sodium hydrogen carbonate solution
  6. dry with materialwith water, dried (MgSO4)
  7. customthe solvent removed by evaporation
  8. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-ceaa673ed9114e78a012af90b9ce2e3d
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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