HCID 69518134, compound → HCID 69465626, compound

HRID 1180011Notes

Reaction equation

HRID 1180011 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11](=[O:20])[N:12]([CH3:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][CH:9]=1)([O-])=O.[H][H]>O1CCCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11](=[O:20])[N:12]([CH3:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 69518134HCID 69518134, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69465626HCID 69465626, compoundYield 103%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl-phenyl-carbamic acid 5-nitro-pyridin-2-yl ester (10.41 g, 38.1 mmol) in tetrahydrofuran (100 mL) was hydrogenated in a Parr apparatus with wet 5% palladium on carbon and 20 psi hydrogen pressure. After 2 hours the solution was filtered over a short pad of Celite, washed thoroughly with ethyl acetate and evaporated in vacuo, yielding title compound (9.51 g, 103% yield) as a thick oil, which solidified upon standing.

Workup

  1. filtrationAfter 2 hours the solution was filtered over a short pad of Celite
  2. washwashed thoroughly with ethyl acetate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-67219feeb3a9483bb7f3b374f844af5a
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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