Sodium hydride → 2,6-Diamino-4,5-dihydronicotinic acid ethyl ester

HRID 2079946Notes

Reaction equation

HRID 2079946 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]([CH2:9][CH2:10][C:11]#[N:12])=[C:6]([NH2:8])[NH2:7])[CH3:2].[H-].[Na+]>O1CCCC1>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH2:9][CH2:10][C:11]([NH2:12])=[N:8][C:6]=1[NH2:7])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 124949064-Cyano-2-diaminomethylene-butyric acid ethyl ester

Product 1

HCID 124949052,6-Diamino-4,5-dihydronicotinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(2-cyanoethyl) 3,3-diaminopropenoic acid ethyl ester described in Preparation Example A-12 (0.55 g, 3 mmol) in tetrahydrofuran (7 mL) was added dropwise to a suspension of sodium hydride (208 mg, 5.2 mmol, 60% in oil) in tetrahydrofuran (7 mL), and the solution was stirred for 19 hours 20 minutes under reflux. After the reaction was completed, the reaction solution was poured into an ice water, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then, concentrated to obtain the title compound as a crude product (0.188 g, 1 mmol, 34%).

Workup

  1. temperatureunder reflux
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-726d491c8b1b4e45895501c7ca7eb87c
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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