Stannous chloride dihydrate → HCID 67497584, compound

HRID 1628225Notes

Reaction equation

HRID 1628225 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:11][C:10]=1[N+:21]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=2)=[CH:11][C:10]=1[NH2:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 67497417HCID 67497417, compound

Product 1

HCID 67497584HCID 67497584, compoundYield 115.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4-(benzyloxy)-3-nitrophenyl)pyridine 13.0 (1.52 g, 4.97 mmol) in ethyl acetate (20 mL) was added tin(II) chloride dihydrate (4.49 g, 19.87 mmol). The mixture was heated to reflux for 2 hours, then quenched with 100 ml 1N NaOH. The resulting mixture was stirred overnight at room temperature, then partitioned between AcOEt and water. The organic phase was dried on MgSO4 and concentrated to afford 2-(benzyloxy)-5-bromobenzenamine 13.D (1.59 g, 115% yield) which was used in the next step without any further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. customquenched with 100 ml 1N NaOH
  4. custompartitioned between AcOEt and water
  5. customThe organic phase was dried on MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-19eb16209e774f2fbb40ab4d885efff4
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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