Sodium Hydroxide → 2,5-Diamino-4-picoline

HRID 1740934Notes

Reaction equation

HRID 1740934 reaction equation
[Sn](Cl)Cl.[NH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-])=O)=[CH:7][N:6]=1.[OH-].[Na+].CO.C(Cl)Cl>Cl>[NH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([NH2:12])=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 2431652-Amino-4-methyl-5-nitropyridineHCID 21226129Dichloromethane methanol

Product 1

HCID 27344282,5-Diamino-4-picoline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tin(II) chloride (4.95 g, 26.12 mmol) in concentrated hydrochloric acid (13.0 mL) was added 2-amino-5-nitro-4-picoline (1.0 g, 6.53 mmol) and heated at 90° C. for 24 h. The reaction was cooled to room temperature, made basic with 5N NaOH, extracted with ethyl acetate, dried (Na2SO4), and evaporated to give a solid. The crude material was subjected to silica gel chromatography using 10% methanol/methylene chloride as eluant to give the title compound.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customto give a solid

Sources & evidence

ORD record
ord-9b08de61d8524b8c8f421278538735c2
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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