Ethylenediamine → HCID 68601740, compound

HRID 1640518Notes

Reaction equation

HRID 1640518 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[C:9]([O:12][CH3:13])[CH:8]=[CH:7]2.[CH2:14]([NH2:17])[CH2:15][NH2:16]>C(Cl)Cl>[CH3:13][O:12][C:9]1[N:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][CH:3]=[C:2]2[NH:16][CH2:15][CH2:14][NH2:17]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 222443958-Chloro-2-methoxy-1,5-naphthyridine

Product 1

HCID 68601740HCID 68601740, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 8-chloro-2-methoxy-1,5-naphthyridine (1.71 g, 8.81 mmol) and ethylenediamine (1.18 mL, 2 eq.) was heated slowly to 80° C. over 1 h and subsequently up to 100° C. for 2 h. After cooling to rt, the yellow solution was taken in DCM and successively washed with NaHCO3. The aq. layer was back extracted with DCM (3 times) and the combined org. layers were concentrated to afford the title intermediate as a pale yellow oil (0.98 g, 51% yield).

Workup

  1. temperatureAfter cooling to rt
  2. washsuccessively washed with NaHCO3
  3. extractionThe aq. layer was back extracted with DCM (3 times)
  4. concentrationlayers were concentrated

Sources & evidence

ORD record
ord-973d97214c57474cac618b88ec5152b3
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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