5-Amino-4-fluoro-2-methylphenol → 4-(2-Fluoro-5-hydroxy4-methylanilino)-6-methoxy-7-(2-methoxyethoxy)quinazoline hydrochloride

HRID 634662Notes

Reaction equation

HRID 634662 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])[C:24]([OH:28])=[CH:23][C:21]=1[NH2:22]>C(O)(C)C>[ClH:1].[F:19][C:20]1[CH:26]=[C:25]([CH3:27])[C:24]([OH:28])=[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 101540985-Amino-4-fluoro-2-methylphenolHCID 107306534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline

Product 1

HCID 212603394-(2-Fluoro-5-hydroxy4-methylanilino)-6-methoxy-7-(2-methoxyethoxy)quinazoline hydrochlorideYield 68.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline (76 mg, 0.28 mmol) and 2-fluoro-5-hydroxy-4-methylaniline (40 mg, 0.28 mmol), (prepared as described for the starting material in Example 8), in isopropanol (2.5 ml) was stirred and heated at reflux for 7 hours. The reaction mixture was allowed to cool and the precipitated product collected by filtration, washed with isopropanol and dried to give 4-(2-fluoro-5-hydroxy4-methylanilino)-6-methoxy-7-(2-methoxyethoxy)quinazoline hydrochloride (79 mg 66%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-704cfdfe521a47edaf4ef9c1466206c1
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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