Hydrochloric Acid → HCID 135513650, compound

HRID 1274069Notes

Reaction equation

HRID 1274069 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=1)[NH:9][C:8]2=[O:21].B(Br)(Br)Br.[OH-].[Na+].Cl.CO>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[NH:9][C:8]2=[O:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 135417258HCID 135417258, compound

Product 1

HCID 135513650HCID 135513650, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Methoxy-2-(4'-methoxyphenyl)quinazolin-4-[3 H]-one (0.2 g, 0.71 mmol) was suspended in a 1.0 M solution of BBr3 in DCM (2.2 ml), to give a yellow suspension, which was gently refluxed for 48 hours. The solvent was directly distilled from the reaction vessel to leave a yellow/brown solid, which was hydrolysed with 10% aq. NaOH solution to give a bright yellow, clear solution. The solution was neutralised with 1.0 M aqueous HCl whereupon a cream precipitate formed, which was collected by filtration. The filtrate was extracted into EtOAc. The organic layers were combined, dried (MgSO4) and filtered. The solvent was removed under vacuum to leave a cream solid. Both products were combined (after comparison by TLC) and recrystallised from methanol (0.08 g, 0.33 mmol, 47%), m.p. 288-290° C.

Workup

  1. customto give a yellow suspension, which
  2. temperaturewas gently refluxed for 48 hours
  3. distillationThe solvent was directly distilled from the reaction vessel
  4. customto leave a yellow/brown solid, which
  5. customto give a bright yellow, clear solution
  6. customformed
  7. filtrationwhich was collected by filtration
  8. extractionThe filtrate was extracted into EtOAc
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customThe solvent was removed under vacuum
  12. customto leave a cream solid

Sources & evidence

ORD record
ord-160939a324544771947ed3296a30dee2
Source dataset
uspto-grants-2000_12
Patent number
US06156739

Reaction notes

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