Hydrochloric Acid → 3-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine

HRID 1845880Notes

Reaction equation

HRID 1845880 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([N+:19]([O-])=O)=[N:15][CH:16]=[CH:17][CH:18]=1)[CH3:11].Cl>C(O)C.[Fe]>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([O:12][C:13]1[C:14]([NH2:19])=[N:15][CH:16]=[CH:17][CH:18]=1)[CH3:11]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 469422963-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

Product 1

HCID 211113963-(1-(2,6-Dichloro-3-fluorophenyl)ethoxy)pyridin-2-amineYield 94%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine (56.7 g, 171 mmol) was dissolved in ethanol (354 mL), 2N HCl (35.4 mL) was added, and iron powder (67.0 g, 1196 mmol) was added portionwise under the cooling of ice bath. After 15 min, it was warmed to 85° C. After 1 h, the reaction liquid was cooled to room temperature, to which was added diatomaceous earth (85 g). After stirring for 15 min, the reaction liquid was sucking filtered using diatomaceous earth. The filtrate was evaporated to dryness under reduced pressure to yield the target product as light yellow solid powder (48.2 g, 160 mmol; yield=94%).

Workup

  1. temperaturecooling of ice bath
  2. waitAfter 1 h
  3. customthe reaction liquid
  4. temperaturewas cooled to room temperature, to which
  5. additionwas added diatomaceous earth (85 g)
  6. customthe reaction liquid
  7. filtrationwas sucking filtered
  8. customThe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-42c4d2523dff4468a0e62abd8972a1e4
Source dataset
uspto-grants-2015_02
Patent number
US08952002B2

Reaction notes

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