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

HRID 2079947Notes

Reaction equation

HRID 2079947 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH2:10][CH2:9][C:8]([NH2:11])=[N:7][C:6]=1[NH2:12])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCCC1>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[N:7][C:6]=1[NH2:12])[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 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-diamino-4,5-dihydronicotinic acid ethyl ester described in Preparation Example A-13 (4.5 g, 24.6 mmol) in tetrahydrofuran (300 mL) was added 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (5.6 g, 24.7 mmol), which was then stirred for 40 minutes at room temperature. The residue obtained by concentrating the reaction solution was then purified by NH silica gel column chromatography (ethyl acetate) to obtain a solid of the target compound. This solid was washed with hexane and dried to obtain the title compound (3.1 g, 17.1 mmol, 69.5%).

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the reaction solution
  3. customwas then purified by NH silica gel column chromatography (ethyl acetate)
  4. customto obtain a solid of the target compound
  5. washThis solid was washed with hexane
  6. customdried

Sources & evidence

ORD record
ord-96d798cf35c1491f96803a8942765e4c
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…