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

HRID 451618노트

반응식

HRID 451618 반응식
[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]

참가 물질

6

반응물 2

HCID 865966735-tert-Butyl-indan-1,2-dione 2-oximeHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 197101995-tert-Butyl-indan-2-ylamine수율 34.4%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 176Acetic Acid용매HCID 1118Sulfuric Acid용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-c4e16f8e35b64e05b71fffa285bd383c
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487116B2

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