Stannous Chloride → HCID 117610971, compound

HRID 588896Notes

Reaction equation

HRID 588896 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([N+:10]([O-])=O)=[CH:4][C:3]=1[CH2:13][C:14]([F:17])([F:16])[F:15].[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>CCO>[Cl:1][C:2]1[C:3]([CH2:13][C:14]([F:16])([F:17])[F:15])=[CH:4][C:5]([NH2:10])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 90455716HCID 90455716, compound

Product 1

HCID 117610971HCID 117610971, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-chloro-5-methoxy-4-nitro-2-(2,2,2-trifluoroethyl)benzene (1.2 g, 4.51 mmol), tin(II) chloride dehydrate (5.0 g, 22.5 mmol) in EtOH (20 mL) was stirred at reflux for 2 h. After cooled to RT, the reaction mixture was added saturated NaHCO3 solution to adjusted pH to 7-8 and then extracted with ethyl acetate. The organic layer washed with brine, dried over Na2SO4 and concentrated in vacuo to afford the desired product (900 mg, 85% yield). 1H NMR (400 MHz, DMSO-d6) δ: 7.29 (s, 1H), 7.11 (s, 1H), 5.41 (s, 2H), 4.21 (s, 3H), 3.99 (dd, J=1.7, 11.2 Hz, 2H).

Workup

  1. temperatureat reflux for 2 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layer washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6239f36ee51e4aab90123a887340c091
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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