5-Amino-2-methylphenol → HCID 21701581, compound

HRID 1596269Notes

Reaction equation

HRID 1596269 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.[OH:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[CH3:26])[NH2:22]>C(O)(C)C>[ClH:2].[OH:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[CH3:26])[NH:22][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 178185-Amino-2-methylphenolHCID 21701573HCID 21701573, compound

Product 1

HCID 21701581HCID 21701581, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-7-(2-methoxyethoxy)quinazoline hydrochloride (450 mg, 1.6 mmol), (prepared as described for the starting material in Example 1), and 3-hydroxy4-methylaniline (280 mg, 2.27 mmol) in isopropanol (20 ml) was heated at reflux for 30 minutes. The solvent was removed by evaporation and the residue was triturated with isopropanol. The resulting solid was collected by filtration, washed with isopropanol and dried under vacuum to give 4-(3-hydroxy4-methylanilino)-7-(2-methoxyethoxy)quinazoline hydrochloride (428 mg, 74%).

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux for 30 minutes
  4. customThe solvent was removed by evaporation
  5. customthe residue was triturated with isopropanol
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with isopropanol
  8. customdried under vacuum

Sources & evidence

ORD record
ord-07a45e43d80e4d1f9d3da95f8cf67e96
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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