Hydrochloric Acid → HCID 12818603, compound

HRID 67949Notes

Reaction equation

HRID 67949 reaction equation
[Na].[C:2]([O:10]CC)(=O)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:13][C:14]1[N:21]=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]#[N:17].Cl>O.C(O)C>[CH2:7]([O:6][C:4]([C:3]1[C:2](=[O:10])[NH:13][C:14]2[C:15]([C:16]=1[NH2:17])=[CH:18][CH:19]=[CH:20][N:21]=2)=[O:5])[CH3:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 8182592-Amino-3-cyanopyridineHCID 5360545Sodium

Product 1

HCID 12818603HCID 12818603, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4.14 g (0.18 g. atom) of sodium in 100 ml. of ethanol was added 28.8 g. (0.18 mole) of diethyl malonate. After stirring at room temperature for 5 minutes, 7.14 g. (0.06 mole) of 2-aminonicotinonitrile was added and the mixture was heated under reflux for 6 hours. The mixture was cooled and was diluted with 100 ml. of water and was acidified with conc. hydrochloric acid. On cooling, a precipitate was formed which was collected and was triturated with 1000 ml. of boiling ethanol. The mixture was filtered and the filtrate was cooled in ice to precipitate 2.9 g. of product, m.p. 264°-267° C. dec.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. temperatureThe mixture was cooled
  4. additionwas diluted with 100 ml
  5. temperatureOn cooling
  6. customa precipitate was formed which
  7. customwas collected
  8. customwas triturated with 1000 ml
  9. filtrationThe mixture was filtered
  10. temperaturethe filtrate was cooled in ice
  11. customto precipitate 2.9 g

Sources & evidence

ORD record
ord-d3e9c6e4cf364e669017d187bd032c5f
Source dataset
uspto-grants-1982_08
Patent number
US04347362

Reaction notes

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