Ammonia → 2,2'-(Ethane-1,2-diyl)di(quinolin-8-ol)

HRID 886766Notes

Reaction equation

HRID 886766 reaction equation
[CH2:1]([C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[C:18]([O:25]C)[CH:19]=[CH:20][CH:21]=2)[N:16]=1)[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([O:13]C)[CH:7]=[CH:8][CH:9]=2)[N:4]=1.[OH-].[Na+].N.[Na+].[Cl-]>Br.CO>[CH2:2]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([OH:13])[CH:7]=[CH:8][CH:9]=2)[N:4]=1)[CH2:1][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[C:18]([OH:25])[CH:19]=[CH:20][CH:21]=2)[N:16]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 10736234HCID 10736234, compound

Product 1

HCID 154560082,2'-(Ethane-1,2-diyl)di(quinolin-8-ol)Yield 97%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 887MethanolSolvent

Procedure

The product has already been described in: C. Kitamura et al., J. Chem. Soc., Perkin Trans. 1 2000, 781-785, from which this stage of synthesis was very slightly altered. It has also been described but obtained by another method of synthesis in: M. Albrecht et al., Synthesis 1999, 10, 1819-1829. A solution of 2,2′-(1,2-ethanediyl)-bis[8-(methyloxy)quinoline] (2.83 g; 8.23 mmol) in 48% hydrobromic acid (150 ml) is heated under reflux for 24 hours. After cooling to ambient temperature, the mixture is neutralised with a 3M aqueous solution of sodium hydroxide, leading to the formation of a green precipitate. The product is extracted with dichloromethane then washed in water and brine. The organic phase is dried over Na2SO4 and the solvent is evaporated under vacuum to yield 7 in the form of a pale green powder (2.53 g; 8.00 mmol, yield=97%). NMR-1H (250 MHz, CDCl3) δ, ppm: 9.35 (s large, 2H); 8.20 (d, 3J (H, H)=8.5 Hz, 2H); 7.53 (d, 3J (H, H)=8.5 Hz, 2H); 7.37 (m, 2H); 7.32 (dd, 3J (H, H)=6.5 Hz, 4J (H, H)=2.0 Hz, 2H); 7.05 (dd, 3J (H, H)=6.5 Hz, 4J (H, H)=2.0 Hz, 2H); 3.57 (s, 4H). MS (CID, NH3) m/z: 317 (MH+). Analysis (%) for C20H16N2O2.0.1NaBr: calculated C, 73.53. H, 4.93. N, 8.58. found C, 73.81. H, 4.73. N, 8.50. UV/vis [CH3OH/20 mM Tris-HCl pH=7.4 containing 150 mM NaCl (1/1, v/v)]: λ nm (ε M−1 cm−1)=204 (71,800), 248 (74,200), 305 (5,200).

Workup

  1. custom1 2000, 781-785, from which this stage of synthesis
  2. customobtained by another method of synthesis in: M
  3. customAlbrecht et al., Synthesis 1999, 10, 1819-1829
  4. temperatureunder reflux for 24 hours
  5. extractionThe product is extracted with dichloromethane
  6. washthen washed in water
  7. dry with materialThe organic phase is dried over Na2SO4
  8. customthe solvent is evaporated under vacuum
  9. customto yield 7 in the form of a pale green powder (2.53 g; 8.00 mmol, yield=97%)

Sources & evidence

ORD record
ord-44d0bbb6c691460998ef22fdd8078df6
Source dataset
uspto-grants-2012_08
Patent number
US08247396B2

Reaction notes

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