5-Amino-2-methylphenol → HCID 21701585, compound

HRID 1596251Notes

Reaction equation

HRID 1596251 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[NH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[OH:26][C:27]1[CH:28]=[C:29]([CH:31]=[CH:32][C:33]=1[CH3:34])[NH2:30]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:30][C:29]3[CH:31]=[CH:32][C:33]([CH3:34])=[C:27]([OH:26])[CH:28]=3)=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 178185-Amino-2-methylphenolHCID 24386Thionyl ChlorideHCID 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-one

Product 1

HCID 21701585HCID 21701585, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-benzyloxy-6-methoxy-3,4-dihydroquinazolin-4-one (5.18 g, 18.4 mmol), (prepared as described for the starting material in Example 4), DMF (1 ml) and thionyl chloride (70 ml) was heated at reflux under argon for 2 hours. The mixture was allowed to cool, excess thionyl chloride was removed by evaporation and the residue azeotroped to dryness with toluene. The resulting crude 7-benzyloxy-4-chloro-6-methoxyquinazoline hydrochloride was suspended in isopropanol (50 ml) and 3-hydroxy4-methylaniline (2.60 g, 21.1 mmol) added. The mixture was heated at reflux for 3 hours and then allowed to cool. The precipitated product was collected by filtration, washed with isopropanol and dried to give 7-benzyloxy-4-(3-hydroxy-4-methylanilino)-6-methoxyquinazoline (4.7 g, 60%).

Workup

  1. custom(prepared
  2. temperaturewas heated
  3. temperatureat reflux under argon for 2 hours
  4. temperatureto cool
  5. customexcess thionyl chloride was removed by evaporation
  6. customthe residue azeotroped to dryness with toluene
  7. temperatureThe mixture was heated
  8. temperatureat reflux for 3 hours
  9. temperatureto cool
  10. filtrationThe precipitated product was collected by filtration
  11. washwashed with isopropanol
  12. customdried

Sources & evidence

ORD record
ord-6358eb56737b43dfa9e7a1d94cc50515
Source dataset
uspto-grants-2001_09
Patent number
US06291455B1

Reaction notes

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