2-Fluoro-4-methylaniline → HCID 21701591, compound

HRID 1596268Notes

Reaction equation

HRID 1596268 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.[F:19][C:20]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:21]=1[NH2:22]>C(O)(C)C>[ClH:1].[F:19][C:20]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:21]=1[NH:22][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

Participants

4

Reactant 2

HCID 679842-Fluoro-4-methylanilineHCID 107306534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline

Product 1

HCID 21701591HCID 21701591, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline (107 mg, 0.4 mmol), (prepared as described for the starting material in Example 14), and 2-fluoro4-methylaniline (50 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 add ether and dried to give 4-(2-fluoro-4-methylanilino)-6-methoxy-7(2-methoxyethoxy)quinazoline hydrochloride (95 mg, 60%) as an off-white solid.

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 2 hours
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with isopropanol
  6. additionadd ether
  7. customdried

Sources & evidence

ORD record
ord-ebcdbc12956d482781854c8a7fbd1fa6
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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