Dimethylformamide dimethyl acetal → HCID 59436197, compound

HRID 1624576Notes

Reaction equation

HRID 1624576 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][N:9]=[C:10]([C:15](=[O:19])[CH2:16][O:17][CH3:18])[C:11]([O:13][CH3:14])=[O:12].[CH3:20]OC(OC)N(C)C>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:20]=[C:16]([O:17][CH3:18])[C:15](=[O:19])[C:10]([C:11]([O:13][CH3:14])=[O:12])=[N:9]1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178496275HCID 178496275, compound

Product 1

HCID 59436197HCID 59436197, compoundYield 90%

Procedure

A solution of methyl 2-[(2-fluorophenyl)hydrazono]-4-methoxy-3-oxobutanoate (5.02 g, 18.7 mmol) in N,N-dimethylformamide dimethyl acetal (35 mL) was refluxed for 1 h. After cooling to room temperature, the precipitate was collected by filtration and washed with hexane/AcOEt (2/1) to give the title compound (4.70 g, 90% yield) as off-white crystals: mp 155-157° C.; 1H NMR (300 MHz, CDCl3): δ ppm 3.91 (3H, s), 3.97 (3H, s), 7.29-7.36 (2H, m), 7.44-7.51 (1H, m), 7.65 (1H, dt, J=1.9, 7.9 Hz), 7.77 (1H, d, J=2.3 Hz). Anal. Calcd for C13H11FN2O4: C, 56.12; H, 3.98; N, 10.07. Found: C, 56.17; H, 3.97; N, 10.25.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with hexane/AcOEt (2/1)

Sources & evidence

ORD record
ord-b9c6b08aa4b847d2b34de2d1bf541963
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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