Acetic Acid → HCID 67417445, compound

HRID 1951372Notes

Reaction equation

HRID 1951372 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=O.[C:15]([CH:17]=[C:18]([O-])[CH3:19])#[N:16].[Na+].[NH2:22][C:23]1[CH:28]=[CH:27][NH:26][C:25](=[O:29])[CH:24]=1.C(O)(=O)C>CC(O)C>[CH3:19][C:18]1[NH:22][C:23]2[CH:28]=[CH:27][NH:26][C:25](=[O:29])[C:24]=2[CH:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:4]=2[O:3][C:2]([CH3:1])=[CH:11][C:10]3=[O:12])[C:17]=1[C:15]#[N:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

Product 1

HCID 67417445HCID 67417445, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

300 mg (1.59 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde are dissolved with 167.5 mg (1.59 mmol) of sodium 1-cyanoprop-1-en-2-olate, 175 mg (1.59 mmol) of 4-aminopyridin-2(1H)-one [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] and 137 μl (2.39 mmol) of acetic acid in 12 ml of 2-propanol and heated under reflux under argon for 12 h. After cooling, the reaction mixture is filtered and the remaining solid is washed with diethyl ether (20 ml). 454 mg (82% of theory) of the title compound are obtained as a white solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 12 h
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture is filtered
  5. washthe remaining solid is washed with diethyl ether (20 ml)

Sources & evidence

ORD record
ord-ffec0a812bfc4b45a581e957f3a639f9
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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