Sodium Hydroxide → 2,6-Diaminonicotinic acid

HRID 1927235Notes

Reaction equation

HRID 1927235 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 100.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,6-Diamino-nicotinic acid ethyl ester (2.0 g) described in Manufacturing Example 10-2-3 was dissolved in ethanol (15 mL), and a 1N aqueous solution of sodium hydroxide (15 mL) was added thereto, after which the solution was refluxed for 2 hours. The reaction mixture was cooled to room temperature, and the ethanol solvent was evaporated under a reduced pressure. The reaction mixture was neutralized with 1N hydrochloric acid at 0° C. The precipitated solids were filtered off to obtain the titled compound (1.7 g).

Workup

  1. temperatureafter which the solution was refluxed for 2 hours
  2. customthe ethanol solvent was evaporated under a reduced pressure
  3. customwas neutralized with 1N hydrochloric acid at 0° C
  4. filtrationThe precipitated solids were filtered off

Sources & evidence

ORD record
ord-472915598c9e467eb9e2971bb6c40068
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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