HCID 59441728, compound → HCID 59441997, compound

HRID 1014336Notes

Reaction equation

HRID 1014336 reaction equation
[CH3:1][N:2]([CH3:20])[C:3](=[O:19])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:17][CH3:18])=[C:11]([N+:14]([O-])=O)[CH:12]=2)[CH2:7][CH2:6]1>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:14][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][N:5]2[CH2:4][C:3]([N:2]([CH3:1])[CH3:20])=[O:19])=[CH:9][C:10]=1[O:17][CH3:18]

Participants

5

Reactant 1

HCID 59441728HCID 59441728, compound

Product 1

HCID 59441997HCID 59441997, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N,N-dimethyl-2-[5-(methyloxy)-6-nitro-2,3-dihydro-1H-indol-1-yl]acetamide (0.16 g, 1.72 mmol) in absolute ethanol (50 mL) and ethyl acetate (5 mL) was hydrogenated overnight at 45 psi with catalytic 10% Pd/C. The catalyst was removed by vacuum filtration through a celite pad which was rinsed with methanol. The filtrate was concentrated under reduced pressure and dried under high vacuum to provide 2-[6-amino-5-(methyloxy)-2,3-dihydro-1H-indol-1-yl]-N,N-dimethylacetamide. This was then carried forward without any further purification.

Workup

  1. customThe catalyst was removed by vacuum filtration through a celite pad which
  2. washwas rinsed with methanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-463022f3a4fa4bca8ce1e85b836ce3a0
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

Loading…