3-Nitrophthalic anhydride → 3-(3-Nitrophthalimido)-3-methylpiperidine-2,6-dione

HRID 651438노트

반응식

HRID 651438 반응식
Cl.[NH2:2][C:3]1([CH3:11])[CH2:9][CH2:8][C:7](=[O:10])[NH:6][C:4]1=[O:5].[N+:12]([C:15]1[CH:25]=[CH:24][CH:23]=[C:17]2[C:18]([O:20][C:21](=O)[C:16]=12)=[O:19])([O-:14])=[O:13].C([O-])(=O)C.[Na+]>C(O)(=O)C>[N+:12]([C:15]1[CH:25]=[CH:24][CH:23]=[C:17]2[C:18]([N:2]([C:3]3([CH3:11])[CH2:9][CH2:8][C:7](=[O:10])[NH:6][C:4]3=[O:5])[C:21](=[O:20])[C:16]=12)=[O:19])([O-:14])=[O:13]

참가 물질

5

반응물 3

HCID 216313-Nitrophthalic anhydrideHCID 517045Sodium AcetateHCID 219282523-Amino-3-methylpiperidine-2,6-dione hydrochloride

생성물 1

HCID 155520373-(3-Nitrophthalimido)-3-methylpiperidine-2,6-dione수율 68%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A stirred mixture of α-amino-α-methylglutarimide hydrochloride (1.2 g, 6.7 mmol), 3-nitrophthalic anhydride (1.3 g, 6.7 mmol), and sodium acetate (0.6 g, 7.4 mmol) in acetic acid (30 mL) was heated to reflux under nitrogen for 6 hours. The mixture then was cooled and concentrated in vacuo. The resulting solid was slurried in water (30 mL) and methylene chloride (30 mL) for 30 min. The suspension was filtered, the solid was washed with methylene chloride, and dried in vacuo (60° C., <1 mm) to afford 1.44 g (68%) of 3-(3-nitrophthalimido)-3-methylpiperidine-2,6-dione as a off-white solid: mp 265-266.5° C.; 1HMR (DMSO-d6) δ11.05 (s, 1H), 8.31 (dd, J=1.1 and 7.9 Hz, 1H), 8.16-8.03 (m, 2H), 2.67-2.49 (m, 3H), 2.08-2.02 (m, 1H), 1.88 (s, 3H); 13C NMR (DMSO-d6) δ172.20, 171.71, 165.89, 163.30, 144.19, 136.43, 133.04, 128.49, 126.77, 122.25, 59.22, 28.87, 28.49, 21.04; HPLC, Water Nova-Pak/C18 column, 4 micron, 1 mL/min, 240 nm, 20/80 CH3CN/0.1% H3PO4(aq), 7.38 min(98%). Anal. Calcd For C14H11N3O6: C, 53.00; H, 3.49; N, 13.24. Found: C, 52.77; H, 3.29; N, 13.00.

후처리

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 6 hours
  3. temperatureThe mixture then was cooled
  4. concentrationconcentrated in vacuo
  5. filtrationThe suspension was filtered
  6. washthe solid was washed with methylene chloride
  7. customdried in vacuo (60° C., <1 mm)

출처 및 근거

ORD 기록
ord-a1b23ec4c5474bf7904903e68dd8ee12
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06281230B1

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