HCID 22715007, compound → HCID 70033118, compound

HRID 352010Notes

Reaction equation

HRID 352010 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.[H][H]>[Pt].C1(C)C=CC=CC=1>[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

5

Reactant 2

HCID 22715007HCID 22715007, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70033118HCID 70033118, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalyst3×HCID 1140TolueneSolvent

Procedure

Toluene (150 ml), 5% platinum on carbon (1.55 g), and N-(2-methylpropyl)-6-methyl-3-nitro-2-phenoxypyridin-4-amine (31.00 g) from Part C were placed in a Parr hydrogenation flask at a hydrogen pressure of 345 kPa for 2 hours with shaking. The reaction was monitored by TLC and HPLC. More 5% platinum on carbon (5 g) was added. After 2 hours, another 4 g of 5% platinum on carbon was added and the reaction was continued overnight. The resulting reaction mixture was filtered, and the solvent was removed from the filtrate under reduced pressure. After one hour the resulting brown oil solidified. NMR analysis of the solid (26.37 g) indicated sufficient purity for carrying the product on to the next step.

Workup

  1. waitthe reaction was continued overnight
  2. customThe resulting reaction mixture
  3. filtrationwas filtered
  4. customthe solvent was removed from the filtrate under reduced pressure
  5. waitAfter one hour the resulting brown oil solidified

Sources & evidence

ORD record
ord-be013c8ed57f4eec9677fe09764a48ff
Source dataset
uspto-grants-2004_06
Patent number
US06743920B2

Reaction notes

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