Hydrochloric Acid → HCID 19864575, compound

HRID 1200027Notes

Reaction equation

HRID 1200027 reaction equation
[Na].[C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[N:12])=[N:9][CH:10]=1)([OH:4])=[O:3].[CH2:13]([CH2:15]N)[OH:14].Cl>CO>[C:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[O:14][CH2:13][CH2:15][N:12]=2)=[N:9][CH:10]=1)([OH:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 27611086-Cyanopyridine-3-carboxylic acidHCID 5360545Sodium2×

Product 1

HCID 19864575HCID 19864575, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

Under a nitrogen atmosphere, sodium (12 mmol) is added to a flask containing 10 ml of anhydrous methanol. After the sodium has dissolved, a solution of 5-carboxy-2-cyano-pyridine (5 mmol) in 5 ml of methanol is added dropwise. The mixture is heated at 50° for 1.5 h. The mixture is allowed to cool and a solution of ethanolamine (10 mmol) in a mixture of 5 ml methanol and 1.5 of concentrated HCl is added dropwise. After addition is complete, the reaction mixture is refluxed for 2 h. The solvent is evaporated, the residue dissolved in 45 ml of hot ethanol, the salts are filtered off and the filtrate on cooling gives crystals of the title compound, m.p. 286°-287°.

Workup

  1. temperatureThe mixture is heated at 50° for 1.5 h
  2. temperatureto cool
  3. additionis added dropwise
  4. additionAfter addition
  5. temperaturethe reaction mixture is refluxed for 2 h
  6. customThe solvent is evaporated
  7. dissolutionthe residue dissolved in 45 ml of hot ethanol
  8. filtrationthe salts are filtered off
  9. temperaturethe filtrate on cooling

Sources & evidence

ORD record
ord-21b7e8d56a9f4b32a1998e0def09bd42
Source dataset
uspto-grants-1990_02
Patent number
US04904675

Reaction notes

Loading…