Acetic Acid → 3-Amino-6-benzyloxy-2-methylaminopyridine

HRID 1599328Notes

Reaction equation

HRID 1599328 reaction equation
[CH2:1]([O:8][C:9]1[N:14]=[C:13]([NH:15][CH3:16])[C:12]([N+:17]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>CO.[Zn]>[NH2:17][C:12]1[C:13]([NH:15][CH3:16])=[N:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 104914986-Benzyloxy-2-methylamino-3-nitropyridine

Product 1

HCID 107281183-Amino-6-benzyloxy-2-methylaminopyridine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

21.4 g of zinc were added to a solution of 8.50 of 6-benzyloxy-2-methylamino-3-nitropyridine (prepared as described in Preparation 92) in 360 ml of methanol, and then 8.5 ml of acetic acid were added dropwise. The resuluting mixture was then stirred at room temperature for one hour. At the end of this time, the reaction mixture was filtered to remove insoluble material. The filtrate was freed from the solvent by distillation under reduced pressure, and the resulting residue was dissolved in ethyl acetate. The solution was washed with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure, to give 7.50 g of the title compound having Rf=0.63 (on silica gel thin layer chromatography using ethyl acetate as the developing solvent).

Workup

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. customto remove insoluble material
  3. distillationThe filtrate was freed from the solvent by distillation under reduced pressure
  4. dissolutionthe resulting residue was dissolved in ethyl acetate
  5. washThe solution was washed with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-c70d37af4b46416a9bb5e5a346f9256e
Source dataset
uspto-grants-1998_04
Patent number
US05739345

Reaction notes

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