Hydrochloric Acid → HCID 13515187, compound

HRID 1274070Notes

Reaction equation

HRID 1274070 reaction equation
B(Br)(Br)Br.C(Cl)Cl.C[O:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[C:17]([CH3:20])[N:16]([CH3:21])[C:15]2=[O:22].[OH-].[Na+].Cl>>[OH:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[C:17]([CH3:20])[N:16]([CH3:21])[C:15]2=[O:22]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 10536180HCID 10536180, compound

Product 1

HCID 13515187HCID 13515187, compoundYield 57.1%

Procedure

A 1.0 M solution of BBr3 in DCM (2.9 ml, 2.9 mmol) was added to 8-methoxy-3-N-methyl-2-methylquinazolin-4-[3 H]-one (0.2 g, 0.98 mmol) to form a yellow suspension, which was gently refluxed for 48 hours. The solvent was directly distilled from the reaction vessel to leave a yellow/green solid, which was hydrolysed with 10% aq. NaOH solution to give a cream suspension. The suspension was neutralised with 1.0 M aqueous HCl and then extracted into EtOAc. The organic layers were combined, dried (MgSO4) and filtered. The solvent was removed under vacuum to leave a pale brown solid (0.18 g, 0.94 mmol, 96% crude yield). The product (0.16 g) was purified by column chromatography, using DCM:MeOH (98:2) as eluent to give a white solid (0.12 g, 0.56 mmol, 57%).

Workup

  1. customto form 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/green solid, which
  5. customto give a cream suspension
  6. extractionextracted into EtOAc
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customThe solvent was removed under vacuum
  10. customto leave a pale brown solid (0.18 g, 0.94 mmol, 96% crude yield)
  11. customThe product (0.16 g) was purified by column chromatography

Sources & evidence

ORD record
ord-a0ce7207753b4231bc43784cb48ccfa4
Source dataset
uspto-grants-2000_12
Patent number
US06156739

Reaction notes

Loading…