Dimethylformamide dimethyl acetal → Methyl 1-(3-bromo-2-fluorophenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylate

HRID 2089825Notes

Reaction equation

HRID 2089825 reaction equation
[Br:1][C:2]1[C:3]([F:20])=[C:4]([NH:8][N:9]=[C:10]([C:15](=[O:19])[CH2:16][O:17][CH3:18])[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][CH:7]=1.[CH3:21]OC(OC)N(C)C>>[Br:1][C:2]1[C:3]([F:20])=[C:4]([N:8]2[CH:21]=[C:16]([O:17][CH3:18])[C:15](=[O:19])[C:10]([C:11]([O:13][CH3:14])=[O:12])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178496273HCID 178496273, compound

Product 1

HCID 59436204Methyl 1-(3-bromo-2-fluorophenyl)-5-methoxy-4-oxo-1,4-dihydropyridazine-3-carboxylateYield 75%

Conditions

Temperature
0 °C

Procedure

A mixture of methyl 2-[(3-bromo-2-fluorophenyl)hydrazono]-4-methoxy-3-oxobutanoate (5.36 g, 15.4 mmol) in N,N-dimethylformamide dimethyl acetal (54 mL) was heated to reflux for 2 h and cooled to 0° C. The precipitates were collected by filtration, washed with hexane and dried to yield the title compound (4.16 g, 75% yield) as a brown solid: 1H NMR (DMSO-d6, 300 MHz): δ ppm 3.80 (3H, s), 3.83 (3H, s), 7.40 (1H, td, J=8.1, 1.1 Hz), 7.75-7.84 (1H, m), 7.94 (1H, ddd, J=8.1, 6.4, 1.7 Hz), 8.60 (1H, d, J=1.9 Hz).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with hexane
  5. customdried

Sources & evidence

ORD record
ord-1fcef2cd9301447f838187e0ba665ca7
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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