HCID 22013736, compound → HCID 22013776, compound

HRID 1532690Notes

Reaction equation

HRID 1532690 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][NH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([NH:12][CH3:13])=[O:11])=[CH:8][C:7]=1[N+:16]([O-])=O>C(OCC)(=O)C.C(O)C.[C].[Pd]>[NH2:16][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:6]=1[NH:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:19])[C:10]([NH:12][CH3:13])=[O:11]

Participants

5

Reactant 1

HCID 22013736HCID 22013736, compound

Product 1

HCID 22013776HCID 22013776, compoundYield 87.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% of palladium-carbon (0.738 g) was added to a solution containing 4-{[2-(dimethylamino)ethyl]amino}-N-methyl-3-nitrobenzamide (3.679 g) in a mixture of ethyl acetate (40 ml) and ethanol (37 ml), and the mixture was stirred for 4.5 hours under a hydrogen gas atmosphere at room temperature. After the catalyst was removed out by filtration, the filtrate was concentrated. The residue, with ethyl acetate added thereto, was washed with 1N sodium hydroxide aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and concentrated, thereby yielding the entitled compound (2.862 g) as brown solid.

Workup

  1. customAfter the catalyst was removed out by filtration
  2. concentrationthe filtrate was concentrated
  3. additionThe residue, with ethyl acetate added
  4. washwas washed with 1N sodium hydroxide aqueous solution and saturated brine successively
  5. dry with materialdried over sodium sulfate anhydride
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-266c1b073c7041498535b829c453d6cb
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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