HCID 20093672, compound → HCID 20093669, compound

HRID 274765Notes

Reaction equation

HRID 274765 reaction equation
[ClH:1].[CH:2]1([NH:8][CH2:9][CH2:10][NH:11][C:12]([C:14]2[CH:23]=[C:22]([N+:24]([O-])=O)[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[O:27][CH3:28])=[O:13])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>C(O)C.[Pd]>[ClH:1].[NH2:24][C:22]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([O:27][CH3:28])=[C:14]([C:12]([NH:11][CH2:10][CH2:9][NH:8][CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)=[O:13])[CH:23]=1

Participants

4

Reactant 1

HCID 20093672HCID 20093672, compound

Product 1

HCID 20093669HCID 20093669, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-[2-(cyclohexylamino)ethyl]-1-methoxy-4-nitro naphthalene-2-carboxamide hydrochloride (0.38 g, 0.001 m) in ethanol (100 ml) was hydrogenated at 60 psi using 5% Pd/C as catalyst for 18 hours. The catalyst was removed by filtration and the solvent removed in vacuo. The product was crystallised from ethanol/ether to give 0.3 g of 4-amino-N-[2-(cyclohexylamino)ethyl]-1-methoxy naphthalene-2-carboxamide hydrochloride, m.p. 250°-252° C.

Workup

  1. customfor 18 hours
  2. customThe catalyst was removed by filtration
  3. customthe solvent removed in vacuo
  4. customThe product was crystallised from ethanol/ether

Sources & evidence

ORD record
ord-e30972abb6cf4b678f54c8cea345c10d
Source dataset
uspto-grants-1995_02
Patent number
US05389684

Reaction notes

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