5-tert-Butyl-indan-1,2-dione 2-oxime → 5-(1,1-Dimethylethyl)-2,3-dihydro-1H-inden-2-amine

HRID 451618Notes

Reaction equation

HRID 451618 reaction equation
[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]

Participants

6

Reactant 2

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

Product 1

HCID 197101995-(1,1-Dimethylethyl)-2,3-dihydro-1H-inden-2-amineYield 34.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-c4e16f8e35b64e05b71fffa285bd383c
Source dataset
uspto-grants-2013_07
Patent number
US08487116B2

Reaction notes

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