Trifluoroacetic anhydride → 5-Bromo-1,2-dihydroquinolin-2-one

HRID 2175211Notes

Reaction equation

HRID 2175211 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N+:7]2[O-].FC(F)(F)C(OC(=O)C(F)(F)F)=[O:16].C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:16])[NH:7]2

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 593983225-Bromo-1-oxo-1lambda~5~-quinoline

Product 1

HCID 142210325-Bromo-1,2-dihydroquinolin-2-oneYield 102.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromoquinoline 1-oxide (2.7 g, 12.05 mmol) in DMF (8 mL) was added trifluoroacetic anhydride (8.51 mL, 60.3 mmol) in three portions at 0° C. The reaction was allowed to warm to room temperature where it stirred overnight. At the conclusion of this period, the reaction mixture was poured into a saturated aq. NaHCO3 (100 mL) solution, and extracted with DCM (2×50 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to afford the title compound (2.76 g, 98% yield) as a light yellow solid. LCMS, [M+H]+=223.9. 1H NMR (400 MHz, DMSO-d6) δ 11.98 (s, 1H), 8.05 (d, J=9.8 Hz, 1H), 7.50 (dd, J=8.0 Hz, 1H), 7.44 (t, J=8.0 Hz, 1H), 7.36 (d, J=8.0 Hz, 1H), 6.63 (d, J=9.8 Hz, 1H).

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f7544daffb9a4894a7ff42d1f0cb8189
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

Loading…