Ethylenediamine → HCID 22034102, compound

HRID 2121614Notes

Reaction equation

HRID 2121614 reaction equation
Br[C:2]1[C:11]2[C:6](=[C:7]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:21])[CH:3]=1.[CH2:22]([NH2:25])[CH2:23][NH2:24]>C(O)CO>[NH2:24][CH2:23][CH2:22][NH:25][C:2]1[C:11]2[C:6](=[C:7]([C:12]3[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[CH3:20])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:21])[CH:3]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 22034106HCID 22034106, compound

Product 1

HCID 22034102HCID 22034102, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

In a sealed tube, heat 4-bromo-2-methyl-8-(2,4,6-trimethyl-phenyl)-quinoline (100 mg, 0.29 mmol) at 140° C. in a mixture of ethylene glycol (1 mL) and ethylene diamine (0.3 mL). After 4 h, cool the reaction mixture and partition between saturated aqueous NaHCO3 and chloroform. Dry the combined organic extracts on Na2SO4 and concentrate under reduced pressure to obtain the title compound as a yellow glass: +APcI MS (M+1)+ 320; 1H NMR (methanol-d4) δ: 7.78 (dd, 1H), 7.39 (t, 1H), 7.34 (dd, 1H), 6.95 (s, 2H), 6.31 (s, 1H), 3.34 (t, 2H), 3.11 (t, 2H), 2.43 (s, 3H), 2.34 (s, 3H), 1.89 (s, 6H).

Workup

  1. temperaturecool the reaction mixture
  2. custompartition between saturated aqueous NaHCO3 and chloroform
  3. customDry the combined organic extracts on Na2SO4
  4. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-627ea7e2b49246c8bca155f058979d88
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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