Acetonitrile → HCID 14390487, compound

HRID 2351590Notes

Reaction equation

HRID 2351590 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][CH2:11][C:12]([NH2:14])=[O:13])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.C(#N)C>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[C:5]([NH:10][CH2:11][C:12]([NH2:14])=[O:13])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 14390485HCID 14390485, compound

Product 1

HCID 14390487HCID 14390487, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[(3-nitro-2-pyridinyl)amino]acetamide (19.6 g, 0.1 mole) in 160 ml of ethyl acetate was hydrogenated over 5% palladium on carbon (2.0 g) at ~55° C. overnight. The reaction mixture was warmed with acetonitrile and filtered through a Celite pad. The pad was washed with hot acetonitrile and the filtrate was evaporated to a solid. A 1.2-g sample of this solid was recrystallized from methanol-acetonitrile to give a light yellow solid, which was dried under high vacuum at room temperature to give 0.4 g, of title compound, m.p. 153°-55° C. with decomposition.

Workup

  1. filtrationfiltered through a Celite pad
  2. washThe pad was washed with hot acetonitrile
  3. customthe filtrate was evaporated to a solid
  4. customA 1.2-g sample of this solid was recrystallized from methanol-acetonitrile
  5. customto give a light yellow solid, which
  6. customwas dried under high vacuum at room temperature
  7. customto give 0.4 g

Sources & evidence

ORD record
ord-60c7b03a8a3147f9b8e4d400bbe23a4c
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

Loading…