N-{2-[2-(methylsulfonyl)ethoxy]ethyl}-3-nitroquinolin-4-amine → N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine

HRID 547288Notes

Reaction equation

HRID 547288 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][O:7][CH2:8][CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[N+:21]([O-])=O)(=[O:4])=[O:3].[H][H]>C(#N)C.[Pt]>[CH3:1][S:2]([CH2:5][CH2:6][O:7][CH2:8][CH2:9][NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][C:12]=1[NH2:21])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 67204193N-{2-[2-(methylsulfonyl)ethoxy]ethyl}-3-nitroquinolin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 86064731N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6342AcetonitrileSolvent

Procedure

Solid Pt/C (0.9 g of 5%) was added to a suspension of N-{2-[2-(methylsulfonyl)ethoxy]ethyl}-3-nitroquinolin-4-amine (9 g, 26.5 mmol) in acetonitrile (133 mL) in a Parr vessel. The vessel was placed on a shaker and then pressurized with hydrogen to 50 psi (3.4×105 Pa). After 3 hours the reaction mixture was purged with nitrogen and then filtered through a layer of CELITE filter agent. The filter cake was washed with acetonitrile (200 mL) until the washes were clear. The filtrate was concentrated under reduced pressure to provide N4-{2-[2-(methylsulfonyl)ethoxy]ethyl}quinoline-3,4-diamine as a yellow oil.

Workup

  1. customAfter 3 hours the reaction mixture was purged with nitrogen
  2. filtrationfiltered through a layer of CELITE filter agent
  3. washThe filter cake was washed with acetonitrile (200 mL) until the washes
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8421fd995ee54c7e9b4cdb1d7ede96f8
Source dataset
uspto-grants-2011_05
Patent number
US07939526B2

Reaction notes

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