Ethanol → 4-(3-Pyrrolidinylpropoxy)benzene-1,2-diamine

HRID 1790717Notes

Reaction equation

HRID 1790717 reaction equation
CO[C:3]1[CH:19]=[C:18]([NH:20]C)[C:17]([N+:22]([O-])=O)=[CH:16][C:4]=1[O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12](NC)=O)C=1.[CH3:25][CH2:26]O>[Pd]>[N:9]1([CH2:10][CH2:11][CH2:6][O:5][C:4]2[CH:16]=[C:17]([NH2:22])[C:18]([NH2:20])=[CH:19][CH:3]=2)[CH2:8][CH2:12][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 702EthanolHCID 131725843{4-[2-Methoxy-4-(methylamino)-5-nitrophenoxy] (2-pyridyl)}-n-methylcarboxamide

Product 1

HCID 210372924-(3-Pyrrolidinylpropoxy)benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution 2-Nitro-4-(3-pyrrolidinylpropoxy)phenylamine 1 in EtOH, Pd/C (0.1 eq) is added. The reaction vessel is repeatedly purged (×3) with nitrogen, and then stirred under a hydrogen atmosphere for 18 h. The product is filtered through a Celite plug, and the plug washed with 25 mL of EtOH, to yield 2. LCMS 236.2 Rt 0.94 min.

Workup

  1. customThe reaction vessel is repeatedly purged (×3) with nitrogen
  2. filtrationThe product is filtered through a Celite plug
  3. washthe plug washed with 25 mL of EtOH
  4. customto yield 2

Sources & evidence

ORD record
ord-d83a7c5eff9f4444938f5ef737900e22
Source dataset
uspto-grants-2006_07
Patent number
US07071216B2

Reaction notes

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