5-Amino-4-fluoro-2-methylphenol → HCID 86756355, compound

HRID 634718Notes

Reaction equation

HRID 634718 reaction equation
Cl.[Cl:2][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.[F:18][C:19]1[CH:25]=[C:24]([CH3:26])[C:23]([OH:27])=[CH:22][C:20]=1[NH2:21]>CC(O)CCC>[ClH:2].[F:18][C:19]1[CH:25]=[C:24]([CH3:26])[C:23]([OH:27])=[CH:22][C:20]=1[NH:21][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

Participants

4

Reactant 2

HCID 101540985-Amino-4-fluoro-2-methylphenolHCID 21701573HCID 21701573, compound

Product 1

HCID 86756355HCID 86756355, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 223862-PentanolSolvent

Procedure

A solution of 4-chloro-7-(2-methoxyethoxy)quinazoline hydrochloride (275 mg, 1 mmol) and 2-fluoro-5-hydroxy4-methylaniline (170 mg, 1.2 mmol), (prepared as described for the starting material in Example 8), in 2-pentanol (5 ml) was heated at reflux for 2 hours. The mixture was allowed to cool and the precipitate was collected by filtration, washed with isopropanol and ether, and dried under vacuum at 70° C. to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-7-(2-methoxyethoxy)quinazoline hydrochloride(295 mg, 78%) as a cream solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with isopropanol and ether
  6. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-e24f5f4f8a51422aa78a33593c1560c1
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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