Nitrogen → HCID 59441925, compound

HRID 1014409Notes

Reaction equation

HRID 1014409 reaction equation
N#N.[CH3:3][N:4]([CH2:6][C:7]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([N:21]([CH3:23])[CH3:22])=[C:15]([N+:18]([O-])=O)[CH:16]=2)[CH2:11][CH2:10]1)=[O:8])[CH3:5]>C(O)C.[Pd]>[CH3:5][N:4]([CH2:6][C:7]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([N:21]([CH3:23])[CH3:22])=[C:15]([NH2:18])[CH:16]=2)[CH2:11][CH2:10]1)=[O:8])[CH3:3]

Participants

5

Reactant 2

HCID 947NitrogenHCID 59441657HCID 59441657, compound

Product 1

HCID 59441925HCID 59441925, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To an N2 degassed solution of 1-[(dimethylamino)acetyl]-N,N-dimethyl-6-nitro-2,3-dihydro-1H-indol-5-amine (1.00 g, 3.42 mmol) and 10% Pd/C (3.64 g, 3.42 mmol) in ethanol (100 ml) was added H2 and the reaction was stirred at rt overnight on the Fisher Porter at 50 psi. The reaction was filtered through celite, rinsed with methanol (100 ml), concentrated by rotary evaporation, and high vacced prior to the next reaction to give the title compound (0.9 g, 100%). ESIMS (M+H)+=263.

Workup

  1. filtrationThe reaction was filtered through celite
  2. washrinsed with methanol (100 ml)
  3. concentrationconcentrated by rotary evaporation, and high vacced
  4. customto the next reaction

Sources & evidence

ORD record
ord-997afe89cf3646609cc233134d47929f
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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