2,3-dimethyl-5-nitro-6-phenoxy-N-[2-(3-pyridin-3-ylpropoxy)ethyl]pyridin-4-amine → 5,6-dimethyl-2-phenoxy-N4-[2-(3-pyridin-3-ylpropoxy)ethyl]pyridine-3,4-diamine

HRID 1008014Notes

Reaction equation

HRID 1008014 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([NH:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[C:5]([N+:22]([O-])=O)=[C:4]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:3]=1.[H][H]>C1(C)C=CC=CC=1.[Pt]>[CH3:8][C:7]1[C:6]([NH:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[C:5]([NH2:22])[C:4]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[N:3][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 219139462,3-dimethyl-5-nitro-6-phenoxy-N-[2-(3-pyridin-3-ylpropoxy)ethyl]pyridin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 691854145,6-dimethyl-2-phenoxy-N4-[2-(3-pyridin-3-ylpropoxy)ethyl]pyridine-3,4-diamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, a solution of 2,3-dimethyl-5-nitro-6-phenoxy-N-[2-(3-pyridin-3-ylpropoxy)ethyl]pyridin-4-amine (27.1 g) in toluene (300 ml) was added to a Parr hydrogenation flask containing 5% platinum on carbon (10 g). After 4 hours at a hydrogen pressure of 207 kPa, the reaction was judged complete by HPLC and TLC analysis. The molecular weight and structure of the product were confirmed by LC/MS and NMR analysis, respectively. The reaction mixture was filtered through filter paper, Celite™, and magnesium sulfate. The filtrate was used in the next step.

Workup

  1. filtrationThe reaction mixture was filtered
  2. filtrationthrough filter paper, Celite™, and magnesium sulfate

Sources & evidence

ORD record
ord-11f1ed88070d44df91f4be74f8c30bc9
Source dataset
uspto-grants-2004_09
Patent number
US06797718B2

Reaction notes

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