Stannous chloride dihydrate → HCID 22144524, compound

HRID 1824779Notes

Reaction equation

HRID 1824779 reaction equation
[Cl:1][C:2]1[C:3]([N+:11]([O-])=O)=[C:4]([OH:10])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.O.O.[Sn](Cl)Cl>C(OCC)(=O)C.[F-].[K+]>[NH2:11][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([O:8][CH3:9])=[CH:5][C:4]=1[OH:10]

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 22144507HCID 22144507, compound

Product 1

HCID 22144524HCID 22144524, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 522689Potassium FluorideSolvent

Procedure

A solution of 3-chloro-5-methoxy-2-nitrophenol [1] (450 mg) and tin(II) chloride dihydrate (2 g, 4 eq.) in ethyl acetate (30 mL) was heated under reflux for 4 h. The mixture was cooled, diluted with ethyl acetate and aqueous potassium fluoride. The mixture was filtered through celite. The organic layer was washed with brine and dried over MgSO4. Evaporation of the solvent afforded the title compound (280 mg) as a pale solid. NMR (DMSO-d6): 9.74 (m, 1H), 6.33 (d, 1H, J=2.4 Hz), 6.30 (d, 1H, J=2.4 Hz), 4.19 (m, 2H), 3.60 (s, 3H).

Workup

  1. temperatureunder reflux for 4 h
  2. temperatureThe mixture was cooled
  3. filtrationThe mixture was filtered through celite
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f0bd9eb419f94fa0b007956a2905b1c6
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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