Ethyl Acetate → HCID 67343145, compound

HRID 1846662Notes

Reaction equation

HRID 1846662 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:16]([N+:17]([O-])=O)=[CH:15][C:14]([Cl:20])=[CH:13][N:12]=2)[CH2:7][CH2:6]1)=[O:4].C(OCC)(=O)C>[Pt]=S.CO>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:16]([NH2:17])=[CH:15][C:14]([Cl:20])=[CH:13][N:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 67341796HCID 67341796, compound

Product 1

HCID 67343145HCID 67343145, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 82861Platinum sulfide (PtS)CatalystHCID 887MethanolSolvent

Procedure

In a round bottom flask is placed 0.20 g (0.039 mmol) of 5% platinum sulfide on carbon. The vessel is evacuated and refilled with argon three times. To the flask is added a solution of 0.50 g (1.7 mmol) of 5′-chloro-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid methyl ester in a 1:1 mixture of ethyl acetate:methanol (30 mL). The mixture is placed under an atmosphere of hydrogen and stirred at room temperature overnight. The mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to provide 0.45 g (quant.) of 3′-amino-5′-chloro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid methyl ester as a dark oil.

Workup

  1. customIn a round bottom flask is placed
  2. customThe vessel is evacuated
  3. additionrefilled with argon three times
  4. filtrationThe mixture is filtered through a pad of diatomaceous earth
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1a423fee1868478f830473914e931c39
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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