Hydrochloric Acid → 5-methylpyridine-3,4-diamine

HRID 1992533Notes

Reaction equation

HRID 1992533 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][N:5]=[CH:4][C:3]=1[CH3:11].Cl>[Fe].C(O)C>[NH2:8][C:7]1[CH:6]=[N:5][CH:4]=[C:3]([CH3:11])[C:2]=1[NH2:1]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 113210624-Amino-5-methyl-3-nitropyridine

Product 1

HCID 102857885-methylpyridine-3,4-diamineYield 60.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 4-amino-3-methyl-5-nitropyridine (1.198 g), iron powder (1.748 g), ethanol (52 mL) and hydrochloric acid (13 mL) was heated to reflux for 3 hours. After cooling to room temperature the ethanol was distilled off and the resulting suspension was diluted with water to 50 mL and the pH was adjusted to 13 by addition of 2N NaOH. Extraction with ethyl acetate (3×70 mL), drying of the combined organic phases of anhydrous sodium sulphate and evaporation of the solvent afforded 0.579 g (60%) of 3,4-diamino-5-methylpyridine.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. distillationwas distilled off
  4. additionthe resulting suspension was diluted with water to 50 mL
  5. additionthe pH was adjusted to 13 by addition of 2N NaOH
  6. extractionExtraction with ethyl acetate (3×70 mL)
  7. dry with materialdrying of the combined organic phases of anhydrous sodium sulphate and evaporation of the solvent

Sources & evidence

ORD record
ord-c20f74c5dba643bb8313bdc716b30fbc
Source dataset
uspto-grants-2010_01
Patent number
US07648998B2

Reaction notes

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