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

HRID 1171185Notes

Reaction equation

HRID 1171185 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 esterYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A tetrahydrofuran (7 mL) solution of 2-(2-cyanoethyl)3,3-diaminopropenoic acid ethyl ester (0.55 g, 3 mmol) described in Production Example 1-1-1 was dropped into a tetrahydrofuran (7 mL) suspension of sodium hydride (208 mg, 5.2 mmol, 60% in oil), which was refluxed while heating and stirring for 19 hours 20 minutes. Following completion of the reaction, the reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated to obtain the title compound (0.188 g, 1 mmol, 34%) as a crude product.

Workup

  1. temperaturewas refluxed
  2. temperaturewhile heating
  3. customcompletion of the reaction
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7b08320711b942fc8911f2316fb40de4
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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