(3-Nitro-7-phenylquinolin-4-yl)-(2-phenoxyethyl)amine → N4-(2-phenoxyethyl)-7-phenylquinoline-3,4-diamine

HRID 9402Notes

Reaction equation

HRID 9402 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:11][CH:10]=[C:9]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:8]=2)([O-])=O>CO.[Pt]>[O:17]([CH2:16][CH2:15][NH:14][C:13]1[C:12]2[C:7](=[CH:8][C:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[NH2:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 21984122(3-Nitro-7-phenylquinolin-4-yl)-(2-phenoxyethyl)amine

Product 1

HCID 69889831N4-(2-phenoxyethyl)-7-phenylquinoline-3,4-diamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A solution of (3-nitro-7-phenylquinolin-4-yl)-(2-phenoxyethyl)amine (7.25 g, 18.8 mmol) in methanol (150 mL) was added to a Parr vessel charged with 5% platinum on carbon (0.84 g), and the reaction was placed under hydrogen pressure (50 psi, 3.4×105 Pa) for three hours. The reaction mixture was filtered through a layer of CELITE filter aid, and the filtrate was concentrated under reduced pressure, dissolved in toluene (2×25 mL), and concentrated under reduced pressure to provide N4-(2-phenoxyethyl)-7-phenylquinoline-3,4-diamine as a yellow semi-solid.

Workup

  1. customfor three hours
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutiondissolved in toluene (2×25 mL)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c6f8ff1a6e6447ae9d0992d40f4400f0
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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