HCID 4197917, compound → N~2~-(4-Methoxyphenyl)pyridine-2,3-diamine

HRID 1942138Notes

Reaction equation

HRID 1942138 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:5][CH:4]=1>CO.O.O.[Sn](Cl)Cl.Cl>[NH2:16][C:15]1[C:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 1

HCID 4197917HCID 4197917, compound

Product 1

HCID 11447232N~2~-(4-Methoxyphenyl)pyridine-2,3-diamineYield 90%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 61436Stannous chloride dihydrateSolvent

Procedure

6.6 g (27 mmol) of 2-(4-methoxyphenyl)amino-3-nitropyridine was dissolved in methanol (150 mL). A solution in which tin (II) chloride dihydrate was dissolved in 12 N hydrochloric acid (40 mL) was prepared, and this solution was added dropwise to the reaction solution at 0° C. over 5 minutes. The reaction solution was returned to room temperature, and then stirred for 3 hours. After confirming the completion of the reaction, the solvent was distilled off under reduced pressure, and water (100 mL) was added. The reaction solution was adjusted to pH 12 using a 10% aqueous solution of sodium hydroxide, subsequently filtered, and extracted with dichloromethane. The obtained organic layer was dried over anhydrous magnesium sulfate, and then the inorganic matter was separated by filtration. The solvent was distilled off under reduced pressure, to obtain 5.2 g (yield: 90%) of 3-amino-2-(4-methoxyphenyl)aminopyridine as orange-colored crystals.

Workup

  1. customwas prepared
  2. additionthis solution was added dropwise to the reaction solution at 0° C. over 5 minutes
  3. customwas returned to room temperature
  4. customthe completion of the reaction
  5. distillationthe solvent was distilled off under reduced pressure, and water (100 mL)
  6. additionwas added
  7. filtrationsubsequently filtered
  8. extractionextracted with dichloromethane
  9. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  10. customthe inorganic matter was separated by filtration
  11. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c20c005df4464e1cbabb3d0d833b0700
Source dataset
uspto-grants-2013_03
Patent number
US08389523B2

Reaction notes

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