Ethylene Glycol → HCID 23130487, compound

HRID 2079940Notes

Reaction equation

HRID 2079940 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[H-].[Na+].[NH2:7][C:8]1[N:16]=[C:15](Cl)[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].N>[Cu]I.C(OCC)C.O>[NH2:7][C:8]1[N:16]=[C:15]([O:3][CH2:2][CH2:1][OH:4])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 222AmmoniaHCID 24758Sodium hydrideHCID 122639922-Amino-6-chloronicotinic acid

Product 1

HCID 23130487HCID 23130487, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

To ethyleneglycol (0.50 mL) was added sodium hydride (70 mg, 1.7 mmol, 60% in oil), catalytic amount of copper(I) iodide and 2-amino-6-chloronicotinic acid (30 mg, 0.17 mmol), which was stirred for 3 hours at 110° C., then, further stirred overnight at 80° C. After cooling, water, diethyl ether and aqueous ammonia was added to the reaction solution, which was then partitioned, the aqueous layer was neutralized with citric acid, then, extracted with dichloromethane. The organic layer was washed with brine, then dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo to obtain the title compound (14 mg).

Workup

  1. customfurther stirred overnight
  2. customat 80° C
  3. temperatureAfter cooling
  4. customwas then partitioned
  5. extractionextracted with dichloromethane
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b0054bc49d344ebc8b35de6bf75ba8fb
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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