4-Bromophthalic anhydride → 5-Bromo-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

HRID 331612

반응식

HRID 331612 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.Cl.[NH2:14][CH:15]1[CH2:21][CH2:20][C:19](=[O:22])[NH:18][C:16]1=[O:17].C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:11][CH:12]=1)[C:6](=[O:8])[N:14]([CH:15]1[CH2:21][CH2:20][C:19](=[O:22])[NH:18][C:16]1=[O:17])[C:9]2=[O:10]

참가 물질

5

반응물 3

HCID 665904-Bromophthalic anhydrideHCID 1345483-Aminopiperidine-2,6-dione hydrochlorideHCID 517045Sodium Acetate

생성물 1

HCID 444356805-Bromo-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione수율 93%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of 4-bromophthalic anhydride (10.0 g, 44.1 mmol), rac-α-aminoglutarimide hydrochloride (7.25 g, 44.0 mmol) and sodium acetate (3.61 g, 44.0 mmol) in acetic acid (150 mL) was heated to reflux overnight. The reaction mixture was cooled to room temperature, and the solvent was evaporated under vacuum. The residue was stirred in water (170 mL) for 3 hours, and the resulting solid was filtered, washed with additional water (80 mL), and dried under vacuum, to afford 13.8 g of 5-bromo-2-(2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione, in 93% yield; 1H NMR (DMSO-d6) δ 2.03-2.10 (m, 1H), 2.43-2.63 (m, 2H), 2.82-2.97 (m, 1H), 5.17 (dd, J=12.8 Hz, J=5.3 Hz, 1H), 7.85-7.88 (d, J=7.9 Hz, 1H), 8.10 (dd, J=7.9 Hz, J=1.7 Hz, 1H), 8.16 (d, J=1.7 Hz, 1H), 11.15 (s, 1H); 13C NMR (DMSO-d6) δ 21.9, 30.9, 49.2, 125.3, 126.4, 128.5, 130.1, 133.2, 137.6, 165.9, 166.4, 169.7, 172.7; Anal. Calcd for C13H9N2O4Br: C, 46.32; H, 2.69; N, 8.31. Found: C, 46.23; H, 2.47; N, 8.41.

후처리

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customthe solvent was evaporated under vacuum
  4. filtrationthe resulting solid was filtered
  5. washwashed with additional water (80 mL)
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-7206bde7fee347afacd58b1abee10f31
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877780B2

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