Acetic Acid → HCID 67418463, compound

HRID 1951386Notes

Reaction equation

HRID 1951386 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])=O.[C:13]([CH:15]=[C:16]([O-])[CH3:17])#[N:14].[Na+].[NH2:20][C:21]1[CH:26]=[CH:25][NH:24][C:23](=[O:27])[CH:22]=1.C(O)(=O)C>C(O)(C)C>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]2[C:22]3[C:23](=[O:27])[NH:24][CH:25]=[CH:26][C:21]=3[NH:20][C:16]([CH3:17])=[C:15]2[C:13]#[N:14])=[C:4]([O:11][CH3:12])[CH:5]=1)#[N:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 166592514-Formyl-3-methoxybenzonitrileHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

Product 1

HCID 67418463HCID 67418463, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.05 g (6.51 mmol) of 4-formyl-3-methoxybenzonitrile are dissolved with 684 mg (6.51 mmol) of sodium 1-cyanoprop-1-en-2-olate, 789 mg (7.16 mmol) of 4-aminopyridin-2(1H)-one [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] and 600 μl (9.77 mmol) of acetic acid in 30 ml of isopropanol and heated under reflux under argon for 12 h. Cooling is followed by filtration, and the remaining solid is washed with diethyl ether (40 ml). 1.96 g (94% of theory) of the title compound are obtained as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 12 h
  3. temperatureCooling
  4. filtrationis followed by filtration
  5. washthe remaining solid is washed with diethyl ether (40 ml)

Sources & evidence

ORD record
ord-c6e4d94148c344c2b3b0285f0186d929
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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