Formic Acid → 3-Benzyl-7-bromoquinazolin-4(3H)-one

HRID 601661Notes

Reaction equation

HRID 601661 reaction equation
[CH2:1]([NH:8][C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1[NH2:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19](O)=O>>[CH2:1]([N:8]1[C:9](=[O:18])[C:10]2[C:11](=[CH:12][C:13]([Br:16])=[CH:14][CH:15]=2)[N:17]=[CH:19]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 122738802-Amino-4-bromo-N-(phenylmethyl)benzamide

Product 1

HCID 231581663-Benzyl-7-bromoquinazolin-4(3H)-one

Procedure

10 ml of formic acid was added to 18.5 g of N-benzyl-2-amino-4-bromobenzamide, and was heated under reflux for 2 hours. After distilling out excess reagent under reduced pressure, saturated sodium bicarbonate aqueous solution was added, and extracted with ethyl acetate. Ethyl acetated layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure, and the residues were separated and purified by silicagel column chromatography (hexane/ethyl acetate=7/3), to obtain 821 mg of the above compound as a colorless solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. distillationAfter distilling out excess reagent under reduced pressure, saturated sodium bicarbonate aqueous solution
  4. additionwas added
  5. extractionextracted with ethyl acetate
  6. washEthyl acetated layer was washed with saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. distillationThe solvents were distilled outunder reduced pressure
  9. customthe residues were separated
  10. custompurified by silicagel column chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-98c001ce092b4c3da5f5b67185aba5af
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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