HCID 22567556, compound → HCID 11736183, compound

HRID 2092516Notes

Reaction equation

HRID 2092516 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][N:5]([CH3:17])[C:6](=[O:16])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1>CO.[Pd]>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH3:18])[CH3:17])=[O:16])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 22567556HCID 22567556, compound

Product 1

HCID 11736183HCID 11736183, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(2-dimethylamino-ethyl)-N-methyl-4-nitro benzamide (4.5 g, 0.0179 mol) in MeOH (100 mL) was added Pd/C 10% (0.5 g) in portions and the Parr reaction vessel was purged with nitrogen for 10 min. The reaction vessel was fixed in Parr shaker at 60 psi pressure for 3 h. The reaction mixture was filtered through the Celite® pad and the filtrate was concentrated under reduced pressure to afford the title compound [4.0 g, 100%]; LC-MS (ESI): Calculated mass: 221.2; Observed mass: 222.1 [M+H]+ (RT: 0.17 min).

Workup

  1. customthe Parr reaction vessel
  2. customwas purged with nitrogen for 10 min
  3. filtrationThe reaction mixture was filtered through the Celite® pad
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-69e45a436a3743c4bd85dcb50a41a5b4
Source dataset
uspto-grants-2013_05
Patent number
US08440662B2

Reaction notes

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