4-Chloro-2-phenylquinazoline → 4-[3-(2-Methoxyphenoxy)-1-pyrrolidinyl]-2-phenylquinazoline

HRID 354796Notes

Reaction equation

HRID 354796 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][CH:6]1[CH2:10][CH2:9][NH:8][CH2:7]1.Cl[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[C:18]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:17]=1>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[O:5][CH:6]1[CH2:10][CH2:9][N:8]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:17]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 809774-Chloro-2-phenylquinazolineHCID 144973553-(2-Methoxyphenoxy)pyrrolidine

Product 1

HCID 127960364-[3-(2-Methoxyphenoxy)-1-pyrrolidinyl]-2-phenylquinazoline

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution containing 150 ml of isopropanol and 4.8 g (0.025 mole) of 3-o-methoxyphenoxypyrrolidine was added, with stirring, 6.15 g (0.025 mole) of 4-chloro-2-phenylquinazoline. The reaction was exothermic and the mixture refluxed for 15 min. The temperature subsided to room temperature and, after standing at room temperature for 11/2 hr, the resulting reaction mixture was filtered. The crystalline solid was recrystallized with isopropanol. Yield of product was 1.9 g, m.p. 142°-144° C.

Workup

  1. additionwas added
  2. temperaturethe mixture refluxed for 15 min
  3. customsubsided to room temperature
  4. customafter standing at room temperature for 11
  5. custom2 hr
  6. customthe resulting reaction mixture
  7. filtrationwas filtered
  8. customThe crystalline solid was recrystallized with isopropanol

Sources & evidence

ORD record
ord-11bf2b6a3953495c91cc7a6d71f68d9f
Source dataset
uspto-grants-1983_03
Patent number
US04377582

Reaction notes

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