Dimethylformamide dimethyl acetal → Methyl 5-methoxy-4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxylate

HRID 1805465Notes

Reaction equation

HRID 1805465 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[O:22])[C:5](=[N:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[CH3:23]OC(OC)N(C)C>>[CH3:1][O:2][C:3]1[C:4](=[O:22])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[N:10][N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)[CH:23]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178496277HCID 178496277, compound

Product 1

HCID 59436268Methyl 5-methoxy-4-oxo-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyridazine-3-carboxylateYield 89%

Procedure

A solution of methyl 4-methoxy-3-oxo-2-{[3-(trifluoromethyl)phenyl]hydrazono}butanoate (14.0 g, 44 mmol) in N,N-dimethylformamide dimethyl acetal (100 mL) was refluxed for 4 h. After cooling to room temperature, the precipitate was collected by filtration and washed with hexane/AcOEt (3/1) to give the title compound (12.9 g, 89% yield) as off-white crystals: mp 169-170° C.; 1H NMR (300 MHz, CDCl3): δ ppm 3.98 (3H, s), 3.99 (3H, s), 7.66-7.74 (2H, m), 7.83-7.89 (2H, m), 7.95 (1H, s). Anal. Calcd for C14H11F3N2O4: C, 51.23; H, 3.38; N, 8.53. Found: C, 51.15; H, 3.47 N, 8.60.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with hexane/AcOEt (3/1)

Sources & evidence

ORD record
ord-dd023e205f3f459a97d9fad26765f744
Source dataset
uspto-grants-2013_01
Patent number
US08354411B2

Reaction notes

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