Ethylenediamine → (2-Aminoethyl)(4-methyl-5-nitro(2-pyridyl))amine

HRID 631810Notes

Reaction equation

HRID 631810 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18]([NH2:21])[CH2:19][NH2:20]>>[CH3:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=[C:2]([NH:20][CH2:19][CH2:18][NH2:21])[CH:7]=1

Participants

4

Reactant 3

HCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 3453642-Chloro-4-methyl-5-nitropyridine

Product 1

HCID 22142401(2-Aminoethyl)(4-methyl-5-nitro(2-pyridyl))amine

Procedure

To 2-chloro-4-methyl-5-nitro-pyridine (250 mg, 1.45 mmol) was added potassium carbonate (320 mg, 2.32 mmol) followed by ethylenediamine (4.2 g, 70 mmol). The mixture turned hot and was filtered after cooling through kieselguhr. The filtrate was concentrated under reduced pressure and purified by column chromatography (silica, gradient of 1 to 10% methanol containing 7N ammonia in DCM) to yield 205 mg (1.04 mmol, 72%) MS(ESI) m/z=197.1 [M+1]+.

Workup

  1. filtrationwas filtered
  2. temperatureafter cooling through kieselguhr
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. custompurified by column chromatography (silica, gradient of 1 to 10% methanol containing 7N ammonia in DCM)
  5. customto yield 205 mg (1.04 mmol, 72%) MS(ESI) m/z=197.1 [M+1]+

Sources & evidence

ORD record
ord-a3aceaac4342478aa919e0ca3058fdfc
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Reaction notes

Loading…