5-tert-Butyl-indan-1,2-dione 2-oxime → 5-tert-Butyl-indan-2-ylamine

HRID 656450ノート

反応式

HRID 656450 の反応式
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=O)[C:9](=[N:15]O)[CH2:8]2)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(O)(=O)C.S(=O)(=O)(O)O>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([NH2:15])[CH2:8]2)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 2

HCID 865966735-tert-Butyl-indan-1,2-dione 2-oximeHCID 178418361HCID 178418361、化合物

生成物 1

HCID 197101995-tert-Butyl-indan-2-ylamine収率 34.4%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 1118Sulfuric Acid溶媒

実験手順

5-tert-Butyl-indan-1,2-dione 2-oxime (11.67 g) was hydrogenated over 10% palladium on carbon catalyst (2.95 g) using a mixture of 233 ml acetic acid and 15.6 ml concentrated sulfuric acid as solvent. The reaction was run at ambient temperature for 17 hours, under 60 psi hydrogen. After removal of catalyst by filtration, the filtrate was quenched by dropwise addition of 30 ml conc. ammonium hydroxide. The quenched mixture was then extracted with ethyl ether, the organic extracts dried with magnesium sulfate, and the solvent removed under vacuum to give 3.50 g of the product which was used without further purification. 1H NMR (300 MHz, CDCl3) 7.17 (m, 3H), 3.84 (m, 1H), 3.14 (m, 2H), 2.67 (m, 2H), 1.31 (s, 9H). MS (CSI) m/e 190 (M+H)+.

後処理

  1. customAfter removal of catalyst
  2. filtrationby filtration
  3. customthe filtrate was quenched by dropwise addition of 30 ml conc. ammonium hydroxide
  4. extractionThe quenched mixture was then extracted with ethyl ether
  5. dry with materialthe organic extracts dried with magnesium sulfate
  6. customthe solvent removed under vacuum

出典と根拠

ORDレコード
ord-c2838e56d9da41e0996c1d801aba9198
出典データセット
uspto-grants-2011_12
特許番号
US08071762B2

反応ノート

読み込み中…