Chlorosuccinimide → 3-(3-Methoxy-4-nitrophenyl)-5,6-dihydrobenzo[d]isoxazol-7(4H)-one

HRID 509451Notes

Reaction equation

HRID 509451 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[CH:6]=[N:7][OH:8].ClN1C(=O)CCC1=O.Br[C:24]1[C:25](=[O:30])[CH2:26][CH2:27][CH2:28][CH:29]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6]2[C:29]3[CH2:28][CH2:27][CH2:26][C:25](=[O:30])[C:24]=3[O:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 109650372-Bromocyclohex-2-en-1-oneHCID 1317332503-Methoxy-4-nitrobenzaldehyde oxime

Product 1

HCID 895435673-(3-Methoxy-4-nitrophenyl)-5,6-dihydrobenzo[d]isoxazol-7(4H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 3-methoxy-4-nitrobenzaldehyde oxime (5.0 g, 25.5 mmol) in DMF (60 ml) at 0° C. was added N-chlorosuccinimide (4.088 g, 30.61 mmol). The reaction mixture was stirred for 15 min at 0° C., and 1.5 hr at ambient temperature. To the reaction flask was added as solids 2-bromocyclohex-2-enone (6.66 g, 38.2 mmol, prepared as in Kowalski, C. J.; Weber, A. E.; Fields, K. W. J. Org. Chem. (1982), 47(26), 5088-93) followed by sodium bicarbonate (4.29 g, 51 mmol), and the mixture was stirred overnight. The reaction mixture was partitioned between water and dichloromethane, the organic phase was washed with water, sat. NaHCO3, and brine. The organic phase was dried over sodium sulfate and concentrated. The residue was chromatographed on silica gel using hexanes/ethyl acetate mixture as eluent to furnish 4.95 g of the title product. 1H NMR (CDCl3) δ: 7.97 (d, J=8.6 Hz, 1H), 7.60 (s, 1H), 7.32 (dd, J=8.4, 1.4 Hz, 1H), 4.05 (s, 3H), 2.99 (t, J=6.1 Hz, 2H), 2.75 (t, J=6.3 Hz, 2H), 2.31 (quin, J=6.3 Hz, 2H).

Workup

  1. custom1.5 hr
  2. customat ambient temperature
  3. custom6.66 g, 38.2 mmol, prepared as in Kowalski, C
  4. stirringthe mixture was stirred overnight
  5. customThe reaction mixture was partitioned between water and dichloromethane
  6. washthe organic phase was washed with water, sat. NaHCO3, and brine
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-00224008748648c1ae97cbdf44af94df
Source dataset
uspto-grants-2015_08
Patent number
US09096582B2

Reaction notes

Loading…