Methylamine → n-Methyl-3-nitropyridin-4-amine

HRID 912

Reaction equation

HRID 912 reaction equation
CO[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10].[CH3:12][NH2:13]>CCO>[CH3:12][NH:13][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 3558324-Methoxy-3-nitropyridine

Product 1

HCID 556016n-Methyl-3-nitropyridin-4-amineYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Conditions

Temperature
140 °C

Procedure

4-Methoxy-3-nitropyridine (8.17 g, 53.0 mmol) was transferred to a bomb in EtOH (5-10 mL). To this was added a solution of methylamine in EtOH (26.4 mL, 8.03M, 0.212 mol). The bomb was sealed and lowered into an oil bath at 120° C. The bath temperature fell to 90° C. and remained that way for 2 hours. The temperature was raised to 140° C. over 0.5 hour and held there 0.5 hour. The contents were transferred to a flask with EtOH (not very soluble) and the solvent was evaporated. Flash chromatography on silica gel with a gradient of CH2Cl2 /CH3OH gave 7.17 g (88%) of 4-methylamino-3-nitropyridine as a yellow solid: mp 155°-158° C.

Workup

  1. customThe bomb was sealed
  2. customlowered into an oil bath at 120° C
  3. customfell to 90° C.
  4. customfor 2 hours
  5. custom(not very soluble) and the solvent was evaporated

Sources & evidence

ORD record
ord-2a0bdad4b0df4772b53e846d39972e90
Source dataset
uspto-grants-1998_03
Patent number
US05723468

Linked notes

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