Dimethylformamide dimethyl acetal → HCID 59436223, compound

HRID 1407133Notes

Reaction equation

HRID 1407133 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[O:18])[C:5](=[N:10][NH:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[CH3:19]OC(OC)N(C)C>C1(C)C=CC=CC=1>[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]=[CH:14][N:15]=[CH:16][CH:17]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178496287HCID 178496287, compound

Product 1

HCID 59436223HCID 59436223, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 4-methoxy-3-oxo-2-(pyridin-4-ylhydrazono)butanoate (18 g, 70 mmol) and N,N-dimethylformamide dimethyl acetal (28 mL, 210 mmol) in toluene (210 mL) was refluxed for 4 h. The mixture was concentrated under reduced pressure to give black crystals. The crystals were washed with 2-propanol/AcOEt (1:4) to give the title compound (8.2 g, 45% yield) as pale yellow crystals: 1H NMR (300 MHz, CDCl3): δ ppm 3.99 (3H, s), 4.00 (3H, s), 7.62 (2H, dd, J=4.5, 1.5 Hz), 8.01 (1H, s), 8.79 (2H, dd, J=4.5, 1.5 Hz).

Workup

  1. temperaturewas refluxed for 4 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto give black crystals
  4. washThe crystals were washed with 2-propanol/AcOEt (1:4)

Sources & evidence

ORD record
ord-51ac7c59435b4a36a2cbf5cb6898b9a8
Source dataset
uspto-grants-2014_12
Patent number
US08916566B2

Reaction notes

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