3-methoxy-4-nitro-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-ylcarbonyl)pent-1-yloxy]phenyl]benzamide → 4-amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamide

HRID 1005581Notes

Reaction equation

HRID 1005581 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[N+:35]([O-])=O)[C:6]([N:8]([CH3:31])[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([N:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1)=[O:23])=[O:7]>C(O)C.C(OCC)(=O)C.[Fe]>[NH2:35][C:34]1[CH:33]=[CH:32][C:5]([C:6]([N:8]([CH3:31])[C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=2[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([N:24]2[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]2)=[O:23])=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 1

HCID 187914403-methoxy-4-nitro-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-ylcarbonyl)pent-1-yloxy]phenyl]benzamide

Product 1

HCID 183549064-amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-yloxy]phenyl]benzamideYield 80.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-methoxy-4-nitro-N-methyl-N-[4-methyl-2-[5-(4methylpiperazin-1-ylcarbonyl)pent-1-yloxy]phenyl]benzamide (6.2 g) and iron powder (3.43 g) in a mixture of ethanol (65 ml) and ethyl acetate (6 ml) was refluxed for 2 hours. After being cooled to ambient temperature, the solution was filtered through a bed of Celite and the filtrate was evaporated in vacuo. The residue was diluted with ethyl acetate and the solution was washed with saturated sodium hydrogen carbonate and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo to give 4-amino-3-methoxy-N-methyl-N-[4-methyl-2-[5-(4-methylpiperazin-1-ylcarbonyl)pent-1-yloxy]phenyl]benzamide (4.7 g ).

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationthe solution was filtered through a bed of Celite
  3. customthe filtrate was evaporated in vacuo
  4. additionThe residue was diluted with ethyl acetate
  5. washthe solution was washed with saturated sodium hydrogen carbonate and brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-d0bf01534a354e1c877963fe618f6459
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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