5-Amino-4-fluoro-2-methylphenol → HCID 21260334, compound

HRID 634658Notes

Reaction equation

HRID 634658 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1.[F:17][C:18]1[CH:24]=[C:23]([CH3:25])[C:22]([OH:26])=[CH:21][C:19]=1[NH2:20]>C(O)(C)C>[ClH:2].[F:17][C:18]1[CH:24]=[C:23]([CH3:25])[C:22]([OH:26])=[CH:21][C:19]=1[NH:20][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 101540985-Amino-4-fluoro-2-methylphenolHCID 220221614-Chloro-6,7-dimethoxyquinazoline hydrochloride

Product 1

HCID 21260334HCID 21260334, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6,7-dimethoxyquinazoline hydrochloride (2.5 g, 9.6 mmol), (prepared as described for the starting material in Example 1 but without the aqueous work up), and 2-fluoro-5-hydroxy-4-methylaniline (1.48 g, 10.5 mmol) in isopropanol (150 ml) was heated at reflux for 2 hours. The mixture was allowed to cool, the solid product collected by filtration, washed with isopropanol and dried to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-6,7-dimethoxyquinazoline hydrochloride (2.2 g, 71 %).

Workup

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

Sources & evidence

ORD record
ord-2b1944534d894770b5485d81794e5581
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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