Acetaldehyde → HCID 14238452, compound

HRID 893049Notes

Reaction equation

HRID 893049 reaction equation
S(=O)(O)[O-].[Na+].[CH:6](=O)[CH3:7].[NH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[C-:16]#[N:17].[Na+]>O>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][CH:6]([CH3:7])[C:16]#[N:17]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 8929Sodium CyanideHCID 104392-AminopyridineHCID 23665763Sodium Bisulfite

Product 1

HCID 14238452HCID 14238452, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To an aqueous solution of sodium bisulfite in an amount of 10.5 g/20 ml H2O, a 44% acetaldehyde solution in an amount of 10 g was added and refluxed with heating for 1 hour. Then, 9.4 g of 2-aminopyridine was added thereto and the reflux with heating was continued for additional 2 hours. Aqueous solution of sodium cyanide was added thereto in an amount of 7 g/10 ml H2O and reacted at 90° C. for 2 hours. The oil layer was separated and cooled to be crystallized (yield 11.6 g). The crystals were recrystallized from ethyl acetate to give α-(2-pyridylamino)propionitrile in an amount of 9 g (in 67% yield).

Workup

  1. temperaturerefluxed
  2. temperaturewith heating for 1 hour
  3. temperaturethe reflux
  4. temperaturewith heating
  5. customThe oil layer was separated
  6. temperaturecooled
  7. customto be crystallized (yield 11.6 g)
  8. customThe crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-586f9be74a294865994d114c94c78135
Source dataset
uspto-grants-1992_06
Patent number
US05120644

Reaction notes

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