Acetic Anhydride → N-(2,3-Dihydro-1H-inden-4-yl)acetamide

HRID 501514

反応式

HRID 501514 の反応式
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][CH2:8]2)([O-])=O.[CH3:13][C:14](OC(C)=O)=[O:15]>CO.N1C=CC=CC=1.[Pd]>[CH2:8]1[C:9]2[C:5](=[C:4]([NH:1][C:14](=[O:15])[CH3:13])[CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:7]1

参加物

6

反応物 2

HCID 7918Acetic AnhydrideHCID 2535784-Nitroindan

生成物 1

HCID 12683814N-(2,3-Dihydro-1H-inden-4-yl)acetamide

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 1049Pyridine溶媒

実験手順

A suspension of commercially available 4-nitroindane (10 g, 61.3 mmol) and 10% Pd/C (1 g) in MeOH (200 mL) was stirred vigorously under an atmosphere of hydrogen overnight at rt. The reaction was filtered through a pad of Celite® and concentrated, and residual solvent was removed by combining the reaction with toluene followed by evaporation. The crude reaction was taken up in pyridine (100 mL), and Ac2O (20 mL) was added and the reaction stirred for 16 h at rt. The reaction was evaporated and the crude product was purified by flash chromatography (5% MeOH in EtOAc/hexane (1:1) to give the title compound (9.12 g).

後処理

  1. filtrationThe reaction was filtered through a pad of Celite®
  2. concentrationconcentrated
  3. customresidual solvent was removed
  4. customthe reaction with toluene
  5. customfollowed by evaporation
  6. customThe crude reaction
  7. stirringthe reaction stirred for 16 h at rt
  8. customThe reaction was evaporated
  9. customthe crude product was purified by flash chromatography (5% MeOH in EtOAc/hexane (1:1)

出典と根拠

ORDレコード
ord-43436305e3184cd889cf48a2116694a2
出典データセット
uspto-grants-2010_08
特許番号
US07772267B2

関連ノート

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