3-nitro-2-phenoxy-N-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinolin-4-amine → 2-phenoxy-N4-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinoline-3,4-diamine

HRID 432710Notes

Reaction equation

HRID 432710 reaction equation
[N+:1]([C:4]1[C:5]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[C:13]=1[NH:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)([O-])=O.[H][H]>C1(C)C=CC=CC=1.[Pt]>[O:27]([C:5]1[C:4]([NH2:1])=[C:13]([NH:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[N:6]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 2

HCID 187601773-nitro-2-phenoxy-N-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinolin-4-amineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 187601982-phenoxy-N4-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinoline-3,4-diamineYield 74%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalyst2×HCID 1140TolueneSolvent

Procedure

A 500 mL Parr bottle was charged with a solution of 3-nitro-2-phenoxy-N-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinolin-4-amine in toluene (150 mL) and 5% Pt/C catalyst (1.1 g), placed on Parr apparatus and charged with hydrogen (˜54 psi, 3.8 Kg/cm2). The reaction was allowed to shake for 4 hours, at which time the reaction was monitored by HPLC. The reaction was not complete. An additional 1.0 g 5% Pt/C catalyst was added to the Parr bottle, it was recharged with hydrogen and shaken overnight. The reaction was then complete. The mixture was filtered through Celite and washed with toluene (500 mL). The filtrate was concentrated to provide 2-phenoxy-N4-[2-(3-pyridin-3-ylpropoxy)ethyl]-5,6,7,8-tetrahydroquinoline-3,4-diamine as a yellow syrup (8.2 g, 74%). TLC (10% MeOH/CH2Cl2, Rf=0.48). Mass-spec M+1=419.2

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with toluene (500 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e00cf6fe9a074888a18a88d83609c868
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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