HCID 22715007, compound → HCID 70033118, compound

HRID 352011Notes

Reaction equation

HRID 352011 reaction equation
[CH3:1][CH:2]([CH3:22])[CH2:3][NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]=1[N+:19]([O-])=O>C1(C)C=CC=CC=1.[Pt]>[CH3:1][CH:2]([CH3:22])[CH2:3][NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]=1[NH2:19]

Participants

4

Reactant 1

HCID 22715007HCID 22715007, compound

Product 1

HCID 70033118HCID 70033118, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent2×

Procedure

N-(2-Methylpropyl)-6-methyl-3-nitro-2-phenoxypyridin-4-amine (530 g) from Part C was dissolved in warm toluene (2.5 L). 5% Platinum on carbon (50 g) wetted with toluene was added to the resulting solution under a nitrogen atmosphere. The resulting mixture was placed in a hydrogenator, flushed multiple times with hydrogen, and filled to a hydrogen pressure of 345 kPa. The reaction was monitored by TLC and HPLC. The reaction mixture turned warn after 30 minutes, and was allowed to cooled to room temperature over 3 hours. The reaction was complete, and the resulting reaction mixture was filtered through a CELITE pad, washed with hot toluene (2 L). The CELITE pad was also washed with isopropyl alcohol. The solvent was removed from the filtrate under reduced pressure, and the resulting black oil was dissolved in dichloromethane. The resulting solution was washed with water (3×1 L), dried with magnesium sulfate, and concentrated under reduced pressure to a green solid (427 g). NMR analysis of the solid indicated sufficient purity for carrying the product on to the next step.

Workup

  1. additionwas added to the resulting solution under a nitrogen atmosphere
  2. customflushed multiple times with hydrogen
  3. additionfilled to a hydrogen pressure of 345 kPa
  4. customthe resulting reaction mixture
  5. filtrationwas filtered through a CELITE pad
  6. washwashed with hot toluene (2 L)
  7. washThe CELITE pad was also washed with isopropyl alcohol
  8. customThe solvent was removed from the filtrate under reduced pressure
  9. dissolutionthe resulting black oil was dissolved in dichloromethane
  10. washThe resulting solution was washed with water (3×1 L)
  11. dry with materialdried with magnesium sulfate
  12. concentrationconcentrated under reduced pressure to a green solid (427 g)

Sources & evidence

ORD record
ord-52f4712847d54cdd9e5aaf20dab87f11
Source dataset
uspto-grants-2004_06
Patent number
US06743920B2

Reaction notes

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