HCID 21913056, compound → HCID 85898859, compound

HRID 1352562Notes

Reaction equation

HRID 1352562 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[C:13]([N+:14]([O-])=O)=[C:12]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:11]=[C:10]([CH3:24])[C:9]=1[CH3:25]>C1(C)C=CC=CC=1.[Pt]>[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]1[C:9]([CH3:25])=[C:10]([CH3:24])[N:11]=[C:12]([O:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:13]=1[NH2:14]

Participants

4

Reactant 1

HCID 21913056HCID 21913056, compound

Product 1

HCID 85898859HCID 85898859, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent2×

Procedure

A solution of N-(5-chloropentyl)-2,3-dimethyl-5-nitro-6-phenoxypyridin-4-amine (30.86 g, 85 mmol) in toluene (200 mL) was added to a Parr vessel containing a mixture of 5% platinum on carbon (25.24 g) and toluene (100 mL). The vessel was placed under hydrogen pressure (30 psi, 2.0×105 Pa) and allowed to shake overnight. The reaction mixture was filtered through a layer of Celite® filter aid. The filtrate was concentrated under reduced pressure to provide 24.97 g of N4-(5-chloropentyl)-5,6-dimethyl-2-phenoxypyridine-3,4-diamine as a thick off white oil.

Workup

  1. additioncontaining
  2. filtrationThe reaction mixture was filtered through a layer of Celite®
  3. filtrationfilter aid
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7b9cbadf4b8448383bc1cc73f5026cd
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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