Hydrochloric Acid → 6-Methoxy-4-methylpyridin-3-amine

HRID 2380244Notes

Reaction equation

HRID 2380244 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([N+:11]([O-])=O)=[CH:6][N:5]=1>C(O)(=O)C>[NH2:11][C:7]1[C:8]([CH3:10])=[CH:9][C:4]([O:3][CH3:2])=[N:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2431692-Methoxy-4-methyl-5-nitropyridine

Product 1

HCID 2431706-Methoxy-4-methylpyridin-3-amineYield 93.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of stannous chloride dihydrate (41 g) and concentrated hydrochloric acid (40 ml) was added slowly to a solution of 2-methoxy-4-methyl-5-nitropyridine (5.1 g) in acetic acid (40 ml), maintaining the temperature below 35° C. The resulting mixture was stirred at room temperature for 2 hours, and then allowed to stand overnight in the refrigerator. The solid was collected and both solid and supernatant were separately basified with a 20% sodium hydroxide solution. The product was extracted with chloroform, combined, dried (anhydrous magnesium sulfate) and concentrated to give 3.9 g of the title compound as a solid, suitable for use in the next reaction.

Workup

  1. temperaturemaintaining the temperature below 35° C
  2. waitto stand overnight in the refrigerator
  3. customThe solid was collected
  4. extractionThe product was extracted with chloroform
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-de23e591afdb4424a5ddb5bca0bf70ac
Source dataset
uspto-grants-1994_11
Patent number
US05366972

Reaction notes

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