Stannous chloride dihydrate → (2-Methyl-5-amino-phenyl)-(5-pyridin-3-yl-oxazol-2-yl)-amine

HRID 1639708Notes

Reaction equation

HRID 1639708 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[NH:11][C:12]1[O:13][C:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:15][N:16]=1.O.O.[Sn](Cl)Cl>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[NH:11][C:12]1[O:13][C:14]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:15][N:16]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 59302880(2-Methyl-5-nitro-phenyl)-(5-pyridin-3-yloxazol-2-yl)-amine

Product 1

HCID 59302870(2-Methyl-5-amino-phenyl)-(5-pyridin-3-yl-oxazol-2-yl)-amineYield 65.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (2-methyl-5-nitro-phenyl)-(5-pyridin-3-yloxazol-2-yl)-amine (600 mg, 2.02 mmol) in ethanol (20 mL) was added tin(II) chloride dihydrate (2.50 g, 10 mmol). The reaction mixture was heated under reflux for 6 h. The mixture was then concentrated, saturated aqueous NaHCO3 was added and the resultant suspension was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous MgSO4 and concentrated. The residue was silica gel column chromatographed (dichloromethane/ethanol:97/3). 350 mg (65%) of (2-methyl-5-amino-phenyl)-(5-pyridin-3-yl-oxazol-2-yl)-amine was obtained as pale yellow powder.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 6 h
  3. concentrationThe mixture was then concentrated
  4. additionsaturated aqueous NaHCO3 was added
  5. extractionthe resultant suspension was extracted with ethyl acetate (3×20 mL)
  6. washThe combined organic layers were washed with brine (20 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated
  9. customchromatographed (dichloromethane/ethanol:97/3)

Sources & evidence

ORD record
ord-9e0225aa4e2542148b040296cee05797
Source dataset
uspto-grants-2012_02
Patent number
US08110591B2

Reaction notes

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