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

HRID 509451노트

반응식

HRID 509451 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-00224008748648c1ae97cbdf44af94df
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096582B2

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