Dimethylformamide dimethyl acetal → HCID 59436189, compound

HRID 1624688Notes

Reaction equation

HRID 1624688 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-72d4d0360be54e3ebf53fc263961b94a
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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