P-Anisidine → 7-Chloro-4-(4'-methoxyanilino)quinazoline

HRID 2059193Notes

Reaction equation

HRID 2059193 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1>C(O)C>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:21][C:18]3[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=3)=[N:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 2418814,7-Dichloroquinazoline

Product 1

HCID 128067747-Chloro-4-(4'-methoxyanilino)quinazolineYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 ml of ethanol were added to a mixture of 4.8 g of 4,7-dichloroquinazoline and 3.0 g of p-anisidine. The resulting mixture was heated, whereupon the solids dissolved and then the mixture immediately solidified. After cooling, the solidified compound was collected and washed with, in turn, ethanol, dilute aqueous sodium hydroxide and water. The resulting crystals were recrystallized from ethanol to give 4.0 g (yield 51%) of the desired Compound No. 9 in the form of pale yellow plates melting at 177°-179° C.

Workup

  1. temperatureThe resulting mixture was heated, whereupon the solids
  2. dissolutiondissolved
  3. temperatureAfter cooling
  4. customthe solidified compound was collected
  5. washwashed with, in turn, ethanol, dilute aqueous sodium hydroxide and water
  6. customThe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-0f811eb0749241399b7be693d36a262f
Source dataset
uspto-grants-1982_03
Patent number
US04322420

Reaction notes

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