Methylamine → HCID 66569551, compound

HRID 1199659Notes

Reaction equation

HRID 1199659 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.CN.[CH3:13][NH:14]N1C=CC=C([N+]([O-])=O)C1>O1CCCC1>[ClH:1].[NH2:8][C:7]1[C:2]([NH:14][CH3:13])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 796132-Chloro-3-nitropyridineHCID 67867989HCID 67867989, compound

Product 1

HCID 66569551HCID 66569551, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-chloro-3-nitro-pyridine (16 g) was dissolved in dry tetrahydrofuran (200 ml). The solution was exposed to gaseous methylamine until the reaction to N-methylamino-3-nitropyridine was completed. The mixture was filtered and the filtrate was evaporated. The yellow residue was dissolved in 96% EtOH (250 ml) and was charged with 5% Pd/C (1 g) and hydrogenated under standard conditions. After completion of the hydrogenation an aqueous solution of hydrochloric acid was added (50 ml,4N), the Pd catalyst was filtered of and the filtrate was evaporated to give the title compound as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe yellow residue was dissolved in 96% EtOH (250 ml)
  4. additionwas charged with 5% Pd/C (1 g)
  5. additionAfter completion of the hydrogenation an aqueous solution of hydrochloric acid was added (50 ml,4N)
  6. filtrationthe Pd catalyst was filtered of and the filtrate
  7. customwas evaporated

Sources & evidence

ORD record
ord-9a815096e4d84ab5858c59dde111549a
Source dataset
uspto-grants-1990_02
Patent number
US04902686

Reaction notes

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