HCID 59441803, compound → HCID 59441666, compound

HRID 1014340Notes

Reaction equation

HRID 1014340 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([N+:17]([O-])=O)=[C:12]([O:15][CH3:16])[CH:13]=2)[CH2:8][CH2:7]1)=[O:5]>C(O)C.[Pd]>[CH3:20][N:2]([CH2:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([NH2:17])=[C:12]([O:15][CH3:16])[CH:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:1]

Participants

4

Reactant 1

HCID 59441803HCID 59441803, compound

Product 1

HCID 59441666HCID 59441666, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N,N-dimethyl-2-[6-(methyloxy)-5-nitro-2,3-dihydro-1H-indol-1-yl]-2-oxoethanamine (0.16 g, 1.72 mmol) in absolute ethanol (50 mL) was maintained under 45 psi H2(g) with catalytic 10% Pd/C for 12 hours. The catalyst was removed by vacuum filtration through a celite pad and rinsed with methanol. The filtrate was concentrated under reduced pressure and dried under high vacuum to provide 1-[(dimethylamino)acetyl]-6-(methyloxy)-2,3-dihydro-1H-indol-5-amine. This was then carried forward without any further purification. ESIMS (M+H)+=250.

Workup

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

Sources & evidence

ORD record
ord-0185c51743a744d6a7d643d11618d78e
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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