Acetic Acid → N-(6-Bromo-1-oxo-2,3-dihydro-1H-inden-5-yl)acetamide

HRID 1267807ノート

反応式

HRID 1267807 の反応式
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Br:14])[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2].C(O)(=[O:17])C>[O-2].[O-2].[O-2].[Cr+6]>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[Br:14])[C:10](=[O:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 176Acetic Acid2 回HCID 104000345-Acetamido-6-bromoindan

生成物 1

HCID 9993147N-(6-Bromo-1-oxo-2,3-dihydro-1H-inden-5-yl)acetamide収率 80%

試薬・触媒・溶媒 1

HCID 10219390chromium (VI) trioxide触媒

反応条件

温度
0 °C

実験手順

To a solution of 5-acetylamino-6-bromoindane (43.0 g, 0.17 mol) in glacial acetic acid (400 mL) at 50°-55° C. was added dropwise a solution of chromium trioxide (70.0 g, 0,7 mol) in 50% aqueous acetic acid (400 mL) over a period of 30 min. After further stirring for 15 min, the mixture was cooled to 0° C. and quenched with 2-propanol (100 mL). Solvent was removed in vacuo. The residue was diluted with water (1 L) and extracted with ethyl acetate (2×500 mL). The combined ethyl acetate layer was washed with 0.5M aqueous NaOH (1 L), brine, dried over anhydrous MgSO4 and concentrated to give 36 g (80%) of the title compound as a light brown solid which was contaminated with about 10% of 5-bromo-6-acetylamino- 1-indanone. 1H NMR (CDCl3); δ8.60 (1H, s), 7.90 (1H, s), 7.90 (1H, s), 3.10 (2H, t), 2.70 (2H, t), 2.30 (3H, s).

後処理

  1. customquenched with 2-propanol (100 mL)
  2. customSolvent was removed in vacuo
  3. additionThe residue was diluted with water (1 L)
  4. extractionextracted with ethyl acetate (2×500 mL)
  5. washThe combined ethyl acetate layer was washed with 0.5M aqueous NaOH (1 L), brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-f43edfce2a4b497f8375aa5de619fa3a
出典データセット
uspto-grants-2003_04
特許番号
USRE038103E1

反応ノート

読み込み中…