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

HRID 331612

反応式

HRID 331612 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7206bde7fee347afacd58b1abee10f31
出典データセット
uspto-grants-2014_11
特許番号
US08877780B2

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