Hydrochloric Acid → HCID 70577554, compound

HRID 354793Notes

Reaction equation

HRID 354793 reaction equation
[C:1]1([C:7]2[N:16]=[C:15](Cl)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:18][CH:19]1[CH2:23][CH2:22][NH:21][CH2:20]1.Cl>C(O)(C)C>[OH2:18].[C:1]1([C:7]2[N:16]=[C:15]([N:21]3[CH2:22][CH2:23][CH:19]([OH:18])[CH2:20]3)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([C:7]2[N:16]=[C:15]([N:21]3[CH2:22][CH2:23][CH:19]([OH:18])[CH2:20]3)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 809774-Chloro-2-phenylquinazolineHCID 982104-Hydroxypyrrolidine

Product 1

HCID 70577554HCID 70577554, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture containing 12 g (0.05 mole) of 2-phenyl 4-chloroquinazoline, 4.3 g (0.05 mole) of 3-hydroxy pyrrolidine and 150 ml of isopropanol was refluxed for 11/2 hrs. The resulting reaction mixture was filtered. The filtrate was adjusted to pH 10 with sodium hydroxide and concentrated under reduced pressure to dryness. The semi-solid residue was recrystallized twice with hot water, a white crystalline solid was obtained. The white crystalline solid was dissolved in aqueous solution adjusted to pH=3 with hydrochloric acid and reprecipitated by adjusting to pH=7.5 using sodium hydroxide. This white crystalline solid was filtered and recrystallized with hot water to yield 7.3 g of the title compound, m.p. 180°-182° C.

Workup

  1. temperaturewas refluxed for 11/2 hrs
  2. customThe resulting reaction mixture
  3. filtrationwas filtered
  4. concentrationconcentrated under reduced pressure to dryness
  5. customThe semi-solid residue was recrystallized twice with hot water
  6. customa white crystalline solid was obtained
  7. dissolutionThe white crystalline solid was dissolved in aqueous solution
  8. customreprecipitated
  9. filtrationThis white crystalline solid was filtered
  10. customrecrystallized with hot water

Sources & evidence

ORD record
ord-2434b0d08db5413db8d9499a85f02c05
Source dataset
uspto-grants-1983_03
Patent number
US04377582

Reaction notes

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