Hydrochloric Acid → HCID 135411211, compound

HRID 1274068Notes

Reaction equation

HRID 1274068 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]([C:19]#[N:20])=[CH:15][CH:14]=1)[NH:9][C:8]2=[O:21].B(Br)(Br)Br.[OH-].[Na+].Cl>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]([C:19]#[N:20])=[CH:15][CH:14]=1)[NH:9][C:8]2=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 135461710HCID 135461710, compound

Product 1

HCID 135411211HCID 135411211, compoundYield 13.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Methoxy-2-(4-cyanophenyl)quinazolin-4-[3 H]-one (0.2 g, 0.72 mmol) was suspended in a 1.0 M solution of BBr3 in DCM (3.6 ml) to give a brown suspension, which was refluxed for 48 hours. The solvent was directly distilled from the reaction vessel to leave a -brown solid, which was hydrolysed with 10% aq. NaOH solution to give a clear, yellow solution. The solution was neutralised with dilute HCl, whereupon a yellow precipitate formed. The reaction mixture was extracted into an excess of EtOAc. The organic layers were combined, dried (MgSO4) and filtered. The solvent was removed under vacuum to leave a cream solid. The product (108 mg) was purified by column chromatography, using DCM:MeOH (95:5) as the eluent, to give a cream solid (26.4 mg, 0.1 mmol), 14%).

Workup

  1. customto give a brown suspension, which
  2. temperaturewas refluxed for 48 hours
  3. distillationThe solvent was directly distilled from the reaction vessel
  4. customto leave a -brown solid, which
  5. customto give a clear, yellow solution
  6. customformed
  7. extractionThe reaction mixture was extracted into an excess of EtOAc
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customThe solvent was removed under vacuum
  11. customto leave a cream solid
  12. customThe product (108 mg) was purified by column chromatography

Sources & evidence

ORD record
ord-b767bc4a88754e508e5999b74c749849
Source dataset
uspto-grants-2000_12
Patent number
US06156739

Reaction notes

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