Sodium Hydroxide → 2,6-Diaminonicotinic acid

HRID 2079948Notes

Reaction equation

HRID 2079948 reaction equation
C([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[N:7][C:6]=1[NH2:12])C.[OH-].[Na+]>C(O)C>[NH2:12][C:6]1[N:7]=[C:8]([NH2:11])[CH:9]=[CH:10][C:5]=1[C:4]([OH:13])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58784252Ethyl 2,6-diaminonicotinate

Product 1

HCID 189772452,6-Diaminonicotinic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,6-Diamino-nicotinic acid ethyl ester described in Preparation Example A-14 (2 g, 11 mmol) was dissolved in ethanol (15 mL), an aqueous solution of 1N sodium hydroxide (15 mL) was added thereto, followed by stirring for 2 hours under reflux. The reaction solution was allowed to room temperature, ethanol was then removed by evaporation, the residue was cooled on an ice bath, then neutralized with 1N hydrochloric acid. The precipitated solid was collected by filtration, washed with water, then, dried to obtain the title compound (1.72 g, 11 mmol, quantitatively).

Workup

  1. temperatureunder reflux
  2. customwas allowed to room temperature
  3. customethanol was then removed by evaporation
  4. temperaturethe residue was cooled on an ice bath
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-8ad1a6113abc4e4e89ebca4505a4d853
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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