Water → HCID 57503079, compound

HRID 2075580Notes

Reaction equation

HRID 2075580 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:14]([O-])=O)[C:8]([O:12][CH3:13])=[C:9]([Cl:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O.O.Cl[Sn]Cl.O>Cl>[C:1]([C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][CH3:13])=[C:7]([NH2:14])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 574185481-Chloro-5-(1,1-dimethylethyl)-2-methoxy-3-nitrobenzene

Product 1

HCID 57503079HCID 57503079, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

5-tert-Butyl-1-chloro-2-methoxy-3-nitro-benzene (157 mg, 0.646 mmol) was dissolved in 3 mL concentrated HCl and SnCl2.2H2O (0.874 g, 3.87 mmol) was added. The reaction was stirred at 90° C. for 2 hrs, after which water was added and the product extracted into diethyl ether. The organic layer was dried over MgSO4 and concentrated. The residue was purified by column chromatography (2/1 Hex/EtOAc) to yield 100 mg of final product. Calculated mass=213. Observed mass=214

Workup

  1. extractionthe product extracted into diethyl ether
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (2/1 Hex/EtOAc)

Sources & evidence

ORD record
ord-cc2ab3d278bf4559be3ae012e5b63fa0
Source dataset
uspto-grants-2011_04
Patent number
US07919617B2

Reaction notes

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