5-Amino-2-methylphenol → HCID 21701565, compound

HRID 1596263Notes

Reaction equation

HRID 1596263 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.[OH:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[CH3:25])[NH2:21]>C(O)(C)C>[ClH:2].[CH3:14][O:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][C:9]=1[O:15][CH3:16])[N:6]=[CH:5][N:4]=[C:3]2[NH:21][C:20]1[CH:22]=[CH:23][C:24]([CH3:25])=[C:18]([OH:17])[CH:19]=1

Participants

4

Reactant 2

HCID 178185-Amino-2-methylphenolHCID 220221614-Chloro-6,7-dimethoxyquinazoline hydrochloride

Product 1

HCID 21701565HCID 21701565, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-chloro-6,7-dimethoxyquinazoline hydrochloride (130 mg, 0.5 mmol), (prepared as described for the starting material in Example 2), and 3-hydroxy-4-methylaniline (62 mg, 0.5 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 and ether and dried to give 6,7-dimethoxy-4-(3-hydroxy-4-methylanilino)quinazoline hydrochloride (98 mg, 56%) 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 and ether
  6. customdried

Sources & evidence

ORD record
ord-20feaba875164eb9a629e6009647a581
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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