4-Nitro-indan-1-one O-methyl-oxime → HCID 55293440, compound

HRID 1818024Notes

Reaction equation

HRID 1818024 reaction equation
CO[N:3]=[C:4]1[C:12]2[C:7](=[C:8]([N+:13]([O-])=O)[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1>C(O)(C(F)(F)F)=O.[Pd]>[CH:4]1([NH2:3])[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([NH2:13])[C:7]=2[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 866237934-Nitro-indan-1-one O-methyl-oxime

Product 1

HCID 55293440HCID 55293440, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4-nitro-indan-1-one O-methyl-oxime (5.31 g, 25.75 mmol) in 50 mL of TFA was mixed with Pd/C (150 mg) and hydrogenated at 50 psi for 14 hours. The resulting mixture was filtered through a pad of celite and the filtrate was concentrated to give the crude title compound, which was used in the next step without further purification. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ 1.90-2.03 (m, 1H), 2.41-2.53 (m, 3H), 2.63-3.18 (m, 2H), 4.65-4.75 (m, 1H), 7.00-7.13 (m, 1H), 7.18-7.27 (m, 2H), 8.31 (s, 2H).

Workup

  1. filtrationThe resulting mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c61744786b6e49c18df7cf3e7974c6dd
Source dataset
uspto-grants-2009_10
Patent number
US07598417B2

Reaction notes

Loading…