Water → HCID 71236580, compound

HRID 920313Notes

Reaction equation

HRID 920313 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N+:13]([O-])=O)=[N:11][CH:12]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].O.O.[Sn](Cl)Cl.O.C([O-])(O)=O.[Na+]>C(O)C>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:19])[F:20]

Participants

6

Reactant 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 71236766HCID 71236766, compound

Product 1

HCID 71236580HCID 71236580, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-(4-chloro-3-(trifluoromethyl)phenoxy)-2-nitropyridine (8 g, 25.1 mmol) in ethanol (100 mL) was added tin (II) chloride dihydrate (56.7 g, 251 mmol). The reaction mixture was stirred at 80° C. for 2 hr. and poured into 500 mL of H2O and adjusted to basic with 10% NaHCO3. Then, the reaction mixture was extracted with 500 mL of EtOAc. The organic layer was separated, and then dried over Na2SO4, and concentrated under reduced pressure to give 5-(4-chloro-3-(trifluoromethyl)-phenoxy)pyridin-2-amine (6 g, 72.9%).

Workup

  1. extractionThen, the reaction mixture was extracted with 500 mL of EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d5a0e33c1d6b465c81eda304001b592b
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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