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

HRID 509451ノート

反応式

HRID 509451 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-00224008748648c1ae97cbdf44af94df
出典データセット
uspto-grants-2015_08
特許番号
US09096582B2

反応ノート

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