Dimethylformamide dimethyl acetal → HCID 59436189, compound

HRID 2089876Notes

Reaction equation

HRID 2089876 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[O:18])[C:5](=[N:10][NH:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[C:6]([O:8][CH3:9])=[O:7].[CH3:19]OC(OC)N(C)C>>[CH3:1][O:2][C:3]1[C:4](=[O:18])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[N:10][N:11]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:19]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178496281HCID 178496281, compound

Product 1

HCID 59436189HCID 59436189, compoundYield 64%

Procedure

A mixture of methyl 4-methoxy-3-oxo-2-(pyridin-3-ylhydrazono)butanoate (52 g, 210 mmol) in N,N-dimethylformamide dimethyl acetal (80 mL, 600 mmol) was refluxed for 30 min. The mixture was allowed to cool to room temperature and stayed at room temperature overnight. The formed crystals were collected by filtration and washed with AcOEt to give the title compound (35 g, 64% yield) as pale yellow crystals: 1H NMR (300 MHz, CDCl3): δ ppm 3.98 (3H, s), 3.98 (3H, s), 7.48-7.54 (1H, m), 7.96 (1H, s), 8.04 (1H, ddd, J=8.4, 2.6, 1.5 Hz), 8.71 (1H, dd, J=4.9, 1.5 Hz), 8.93 (1H, d, J=2.6 Hz).

Workup

  1. temperaturewas refluxed for 30 min
  2. filtrationThe formed crystals were collected by filtration
  3. washwashed with AcOEt

Sources & evidence

ORD record
ord-628cd417140444eb9d1cbfa42fdcee02
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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