Ethylenediamine → HCID 68601740, compound

HRID 1640546Notes

Reaction equation

HRID 1640546 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 (commercial; 1.7 g, 8.80 mmol) and ethane-1,2-diamine (1.2 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 up in DCM and successively washed with sat. aq. NaHCO3. The org. layer was concentrated under reduced pressure to afford the title intermediate as a pale yellow oil (981 mg, 51% yield).

Workup

  1. temperatureAfter cooling to rt
  2. washsuccessively washed with sat. aq. NaHCO3
  3. concentrationlayer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-806e442c4a434d4698c807bbab7c71bb
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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