2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Ethyl 2,6-diaminonicotinate

HRID 1927234Notes

Reaction equation

HRID 1927234 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:11][CH2:10][C:9]([NH2:12])=[N:8][C:7]=1[NH2:13])=[O:5])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1COCC1>[CH2:1]([O:3][C:4](=[O:5])[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[N:8][C:7]=1[NH2:13])[CH3:2]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 124949052,6-Diamino-4,5-dihydronicotinic acid ethyl ester

Product 1

HCID 58784252Ethyl 2,6-diaminonicotinateYield 69.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of THF (300 mL) and 2,6-diamino-4,5-dihydro-pyridin-3-carboxylic acid ethyl ester (4.5 g) described in Manufacturing Example 10-2-2 was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (5.6 g), which was stirred for 40 minutes at room temperature. The solvent was evaporated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate), after which it was washed with hexane to obtain the titled compound (3.1 g).

Workup

  1. customThe solvent was evaporated under a reduced pressure
  2. customthe residue was purified by NH silica gel column chromatography (ethyl acetate)
  3. washafter which it was washed with hexane

Sources & evidence

ORD record
ord-70289d0927f543a2b04cab13ee2fe6a2
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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