Sodium Hydroxide → 2,6-Diaminonicotinic acid

HRID 1171186Notes

Reaction equation

HRID 1171186 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 acidYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,6-diamino-nicotinic acid ethyl ester (2 g, 11 mmol) described in Production Example 1-1-3 was dissolved in ethanol (15 mL) followed by the addition of 1 N aqueous sodium hydroxide solution (15 mL) and stirring for 2 hours while heating under reflux. After allowing the reaction mixture to return to room temperature, the ethanol was distilled off under a reduced pressure and the residue was cooled with ice and neutralized with 1 N hydrochloric acid. After filtering the precipitated solid and washing with water, the solid was dried to obtain the title compound (1.72 g, 11 mmol, quantitative).

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. customto return to room temperature
  4. distillationthe ethanol was distilled off under a reduced pressure
  5. temperaturethe residue was cooled with ice and neutralized with 1 N hydrochloric acid
  6. filtrationAfter filtering the precipitated solid
  7. washwashing with water
  8. customthe solid was dried

Sources & evidence

ORD record
ord-576960135e6b46c29667252811bea199
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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