Hydrochloric Acid → HCID 10516606, compound

HRID 1055632Notes

Reaction equation

HRID 1055632 reaction equation
O=[C:2]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][C:4]#[N:5].[CH2:12]([O:14][CH:15]([O:19][CH2:20][CH3:21])[CH2:16][NH:17][NH2:18])[CH3:13].Cl>C(O)C.C(OCC)(=O)C>[CH2:12]([O:14][CH:15]([O:19][CH2:20][CH3:21])[CH2:16][N:17]1[C:4]([NH2:5])=[CH:3][C:2]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[N:18]1)[CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 322952(2,2-Diethoxyethyl)hydrazineHCID 157315343-Oxo-3-(3-pyridinyl)propanenitrile

Product 1

HCID 10516606HCID 10516606, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

With gentle heating, 125 g (812 mmol, purity 95%) of 3-oxo-3-(pyridin-3-yl)propionitrile [lit. for example: P. Seneci et al., Synth. Commun. 1999, 29 (2), 311-341; also available commercially] were dissolved in 1.25 liters of ethanol. 126 g (853 mmol) of (2,2-diethoxyethyl)hydrazine and 4.1 ml (4.06 mmol) of 1 M hydrochloric acid were then added. The reaction mixture was heated under reflux for 4 h, and all volatile components were then substantially removed on a rotary evaporator. The residue obtained was taken up in ethyl acetate, and the solution was washed with water and dried over anhydrous magnesium sulphate. After filtration, the mixture was evaporated to dryness. The residue that remained was triturated with diisopropyl ether at RT. The resulting solid was then filtered off with suction and dried under high vacuum. This gave 153 g (65% of theory, purity 96%) of the title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 h
  3. customall volatile components were then substantially removed on a rotary evaporator
  4. customThe residue obtained
  5. washthe solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationAfter filtration
  8. customthe mixture was evaporated to dryness
  9. customThe residue that remained was triturated with diisopropyl ether at RT
  10. filtrationThe resulting solid was then filtered off with suction
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-e2302c1c41a74588b06ed5ae64fd234e
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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