HCID 21882767, compound → HCID 21882746, compound

HRID 722062Notes

Reaction equation

HRID 722062 reaction equation
C([NH:8][C:9]1[C:14]([N+:15]([O-])=O)=[C:13]([O:18][CH2:19][CH2:20][O:21][CH3:22])[CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>CO.Cl.[Pd]>[NH2:8][C:9]1[C:14]([NH2:15])=[C:13]([O:18][CH2:19][CH2:20][O:21][CH3:22])[CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 1

HCID 21882767HCID 21882767, compound

Product 1

HCID 21882746HCID 21882746, compoundYield 78.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

1.87 g of 2-benzylamino-4-(2-methoxyethoxy)-3-nitropyridine (starting material J2) are dissolved in a mixture of 30 ml of methanol and 6.16 ml of 2N aqueous hydrochloric acid and hydrogenated over 500 mg of 10% strength Pd on carbon at 50° C. for 5 hours. After filtration and addition of 6.16 ml of 2N aqueous sodium hydroxide solution the mixture is evaporated to dryness and the residue is chromatographed on silica gel (dichloromethane/methanol 25:1+1% triethylamine). Concentration of the pure fractions and drying in vacuo gives 0.89 g of the title compound as a brownish oil. The mass spectrum shows the molecular peak M+ at 184.0 Da.

Workup

  1. filtrationAfter filtration and addition of 6.16 ml of 2N aqueous sodium hydroxide solution the mixture
  2. customis evaporated to dryness
  3. customthe residue is chromatographed on silica gel (dichloromethane/methanol 25:1+1% triethylamine)
  4. customConcentration of the pure fractions and drying in vacuo

Sources & evidence

ORD record
ord-353bfd5c3d5143a3ac0585a9d9a7aac4
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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