Trifluoroacetic anhydride → 8-Bromoisoquinolin-1(2H)-one

HRID 1437357Notes

Reaction equation

HRID 1437357 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N+:9]([O-])[CH:8]=[CH:7]2.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:16]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:16])[NH:9][CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 687005028-Bromoisoquinoline 2-oxide

Product 1

HCID 529877478-Bromoisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of (a) (630 mg, 2.8 mmol) in DMF (10 ml) was treated with trifluoroacetic acid anhydride (4 ml). The clear solution was stirred at room temperature overnight then evaporated. The residue was treated with dilute aqueous sodium carbonate solution and extracted several times with 5% methanol/dichloromethane. The combined organic extracts were washed with brine, dried and evaporated. The crude product was chromatographed on silica eluting with 0-10% methanol in dichloromethane affording a white solid (180 mg, 29%).

Workup

  1. customthen evaporated
  2. additionThe residue was treated with dilute aqueous sodium carbonate solution
  3. extractionextracted several times with 5% methanol/dichloromethane
  4. washThe combined organic extracts were washed with brine
  5. customdried
  6. customevaporated
  7. customThe crude product was chromatographed on silica eluting with 0-10% methanol in dichloromethane affording a white solid (180 mg, 29%)

Sources & evidence

ORD record
ord-b1a18a6a42b64951901f50a23ac55719
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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