Ammonium Acetate → HCID 178510337, compound

HRID 506171Notes

Reaction equation

HRID 506171 reaction equation
CN(C)C=[CH:4][C:5](=[O:13])[C:6](=[CH:9][N:10](C)[CH3:11])[C:7]#[N:8].C([O-])(=O)C.[NH4+]>CCO>[OH:13][C:5]1[C:6]([C:7]#[N:8])=[CH:9][N:10]=[CH:11][CH:4]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 722970555-(Dimethylamino)-2-(dimethylaminomethylidene)-3-oxopent-4-enenitrile

Product 1

HCID 178510337HCID 178510337, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(dimethylamino)-2-[(dimethylamino)methylene]-3-oxopent-4-enenitrile (64.3 g, 333 mmol) and ammonium acetate (126 g, 1.66 mol) in EtOH (1.8 L) was heated at reflux for 60 h and concentrated to remove solvent. The resultant semi-solid residue was diluted with EtOAc, filtered and washed with EtOAc followed by CH2Cl2. The filtrate was evaporated to a reduced volume. The precipitated solids were collected by filtration, washed with EtOAc and a minimum amount of EtOH. The process of evaporation and crystallization was repeated to obtain more solid product from the mother liquor. The combined off-white solids provided 20.9 g of 4-hydroxynicotinonitrile (53%); melting range: 234-236° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 h
  3. concentrationconcentrated
  4. customto remove solvent
  5. additionThe resultant semi-solid residue was diluted with EtOAc
  6. filtrationfiltered
  7. washwashed with EtOAc
  8. customThe filtrate was evaporated to a reduced volume
  9. filtrationThe precipitated solids were collected by filtration
  10. washwashed with EtOAc
  11. customThe process of evaporation and crystallization
  12. customto obtain more solid product from the mother liquor

Sources & evidence

ORD record
ord-6ad448747f4742d0b3c9df50a2efa317
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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