Methylamine → HCID 66569551, compound

HRID 2351321Notes

Reaction equation

HRID 2351321 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 (16g) was dissolved in dry tetrahydrofuran (200ml). The solution was exposed to gaseous methylamine untill 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 (250ml) 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 (5Oml,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 (250ml)
  4. additionwas charged with 5% Pd/C (1 g)
  5. additionAfter completion of the hydrogenation an aqueous solution of hydrochloric acid was added (5Oml,4N)
  6. filtrationthe Pd catalyst was filtered of and the filtrate
  7. customwas evaporated

Sources & evidence

ORD record
ord-8d15c47b4d114c8aaa3c525a8723cb32
Source dataset
uspto-grants-1989_10
Patent number
US04873244

Reaction notes

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