Ethylenediamine → HCID 89825769, compound

HRID 631837Notes

Reaction equation

HRID 631837 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[N:3]=1.[CH2:11]([NH2:14])[CH2:12][NH2:13].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:13][CH2:12][CH2:11][NH2:14])[CH:7]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 8471TriethylamineHCID 889076561227574-23-3

Product 1

HCID 89825769HCID 89825769, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

2-Bromo-6-methyl-4-methoxy-pyridine (202 mg, 1 mmol) was combined with 1,2-ethylenediamine (3 ml) and triethylamin (280 μl, 2 mmol) and heated in a sealed tube at 120° C. for three hours under microwave heating. The mixture was diluted with ethyl acetate, filtered through kieselguhr and evaporated under reduced pressure. The residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 2% to 100% acetonitrile) to yield 44 mg of a solid (0.24 mmol, 24%) MS(ESI) m/z=182.1 [M+1]+.

Workup

  1. temperatureheating
  2. filtrationfiltered through kieselguhr
  3. customevaporated under reduced pressure
  4. customThe residue was purified by preparative HPLC (Waters XBridge, gradient of water containing 0.1% NH3 and 2% to 100% acetonitrile)

Sources & evidence

ORD record
ord-39d548df8a1f4538bec39f08e38c7b0e
Source dataset
uspto-grants-2016_04
Patent number
US09321724B2

Reaction notes

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