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

HRID 1927233Notes

Reaction equation

HRID 1927233 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:15])[C:7](=[C:12]([NH2:14])[NH2:13])[CH2:8][CH2:9][C:10]#[N:11])[CH3:4]>C1COCC1>[CH2:3]([O:5][C:6]([C:7]1[CH2:8][CH2:9][C:10]([NH2:11])=[N:14][C:12]=1[NH2:13])=[O:15])[CH3:4]

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 34.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of THF (7 mL) and NaH (210 mg/60% in oil) was added dropwise a solution of THF (7 mL) and 4-cyano-2-diaminomethylene-butyric acid ethyl ester (0.55 g) described in Manufacturing Example 10-2-1, which was refluxed for 19 hours and 20 minutes. The reaction solution was poured into ice water and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, after which the solvent was evaporated under a reduced pressure to obtain the crude titled compound (0.19 g).

Workup

  1. temperaturewas refluxed for 19 hours and 20 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-8ac65dab0bd542bcb47fb687edd02869
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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