HCID 58279171, compound → Ethyl 4,5-diaminopyridine-3-carboxylate

HRID 85142Notes

Reaction equation

HRID 85142 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[C:10]([NH2:11])=[C:9]([N+:12]([O-])=O)[CH:8]=[N:7][CH:6]=1)[CH3:2].[H][H]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[C:10]([NH2:11])=[C:9]([NH2:12])[CH:8]=[N:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 58279171HCID 58279171, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58278930Ethyl 4,5-diaminopyridine-3-carboxylateYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture containing 4-amino-5-nitro-nicotinic acid ethyl ester (78; 15 g, 0.071 mol) and 10% Pd/C (500 mg) in MeOH (500 mL) was stirred under 1 atm of hydrogen at room temperature for 18 h. The reaction mixture filtered through a pad of Celite and the filtrate was concentrated under reduced pressure to afford 4,5-diamino-nicotinic acid ethyl ester 79 (10 g, 80%).

Workup

  1. filtrationThe reaction mixture filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-58233bffd883457c9aa99cc62797ea2a
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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