HCID 14882823, compound → HCID 15086594, compound

HRID 359083Notes

Reaction equation

HRID 359083 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:23][CH:24]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 14882823HCID 14882823, compound

Product 1

HCID 15086594HCID 15086594, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methanol (200 ml) and methyl 4-[3-[N-(4nitrophenyl)amino]propoxy]benzoate (6.9 g) were added to 5 % palladium/carbon (0.7 g) and catalytic reduction was carried out at room temperature overnight. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure, then, to the residue was added isopropyl ether. The insoluble product was collected by filtration to give methyl 4-[3-[N-(4-aminophenyl)amino]propoxy]benzoate (5.5 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionto the residue was added isopropyl ether
  4. filtrationThe insoluble product was collected by filtration

Sources & evidence

ORD record
ord-47e04d4a15bb4fee9d9d42a2195e25f0
Source dataset
uspto-grants-1991_03
Patent number
US04999378

Reaction notes

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