Hydrochloric Acid → (2,6-Difluoro-4-methoxy-phenyl)-hydrazine hydrochloride

HRID 537586Notes

Reaction equation

HRID 537586 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([F:10])[C:3]=1[N:11](C(OC(C)(C)C)=O)[NH:12]C(OC(C)(C)C)=O.O1CCOCC1.C(OCC)C.[ClH:38]>>[ClH:38].[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([F:10])[C:3]=1[NH:11][NH2:12]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 68157167Di-tert-butyl 1-(2,6-difluoro-4-methoxyphenyl)hydrazine-1,2-dicarboxylate

Product 1

HCID 68156785(2,6-Difluoro-4-methoxy-phenyl)-hydrazine hydrochloride

Procedure

Di-tert-butyl 1-(2,6-difluoro-4-methoxyphenyl)hydrazine-1,2-dicarboxylate (616 mg, 1.64 mmol) was heated in 4 M HCl in dioxane (5 mL, 20 mmol) at reflux. The solution over time became a suspension. At 30 min, the reaction was cooled, diethylether was added, and the solid was collected with a medium frit, washing with diethylether. This gave (2,6-difluo-4-methoxy-phenyl)-hydrazine hydrochloride (0.246 g, 86%) as a tan solid. 1H NMR (400 MHz, DMSO-d6, δ): 9.75 (br. s., 3H) 7.46 (s, 1H) 6.79-6.90 (m, 2H) 3.78 (s, 3H).

Workup

  1. temperatureat reflux
  2. temperaturethe reaction was cooled
  3. customthe solid was collected with a medium frit
  4. washwashing with diethylether

Sources & evidence

ORD record
ord-394619cb18b34fa882f6f25faba269af
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

Loading…