Ethanol → Ruthenium bis(2,2'-bipyridine) (2,2'-bipyridine-4,4'-dicarboxylic acid) bis(hexafluorophosphate)

HRID 2680Notes

Reaction equation

HRID 2680 reaction equation
OC[C:3]1([CH2:15][OH:16])[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:4]1.[OH2:17].[OH2:18].[Ru+2:19].[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.[F:32][P-:33]([F:38])([F:37])([F:36])([F:35])[F:34].[NH4+].[CH2:40]([OH:42])C>>[F:32][P-:33]([F:38])([F:37])([F:36])([F:35])[F:34].[F:32][P-:33]([F:38])([F:37])([F:36])([F:35])[F:34].[N:10]1[CH:11]=[CH:12][C:13]([C:40]([OH:42])=[O:17])=[CH:14][C:9]=1[C:5]1[CH:4]=[C:3]([C:15]([OH:16])=[O:18])[CH:8]=[CH:7][N:6]=1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.[N:6]1[CH:7]=[CH:8][CH:3]=[CH:4][C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[Ru+2:19]

Participants

5

Reactant 4

HCID 702EthanolHCID 9793912Ammonium hexafluorophosphateHCID 701425084,4-Di(hydroxymethyl)-2,2'-bipyridineHCID 131720582HCID 131720582, compound

Product 1

HCID 15381271Ruthenium bis(2,2'-bipyridine) (2,2'-bipyridine-4,4'-dicarboxylic acid) bis(hexafluorophosphate)

Procedure

4,4'-Diethoxycarbonyl-2,2'-bipyridine was prepared from 2,2-bipyridine-4,'dicarboxylic acid by the method of Sprintschink et al. (J. Amer. Chem. Soc. 99, 4947 (1977)). The diethyl ester (100 mg) was dissolved in anhydrous diethyl ether (35 ml). Lithium aluminum hydride (100 mg) was added, and following a 30 minute incubation diethyl ether (35 ml) and ice cold deionized water (100 ml) were added. The solution was mixed throughly and the ether layer collected. The aqueous phase was extracted twice more with ether (70 ml). The combined ether extracts were dried over anhydrous sodium sulfate and filtered. The solvent was removed on a rotary evaporator to give the desired product (43 mg). This 43 mg of 4,4-Di(hydroxymethyl)-2,2'-bipyridine and 120 mg of cisdichloro his (2,2'-bipyridine) ruthenium (II) dihydrate were added to ethanol (25 ml), and the solution was refluxed for 14 hours. After the solution had cooled, 50 ul of solution of ammonium hexafluorophosphate (1 gm in 1 ml of water) was added, the resultant crystalline solid was collected, washed with a small volume of ethanol and dried to give 138 mg of the hexafluorophosphate salt of the 4,4-dihydroxymethyl complex. This complex (6 mg) was added to thionyl chloride (5 ml), and the solution was refluxed for 6 hours. The thionyl chloride was removed by distillation, and the solid residue was dissolved in a dioxane-water (1:1) mixture (500 ul). This solution containing 4,4'-(dichloromethyl)-2,2'-bipyridyl, bis(2,2'bipyridyl) ruthenium (II) was used for labeling of antibody.

Workup

  1. temperaturethe solution was refluxed for 14 hours
  2. temperatureAfter the solution had cooled
  3. customthe resultant crystalline solid was collected
  4. washwashed with a small volume of ethanol
  5. customdried

Sources & evidence

ORD record
ord-4650456a153c455f9e0bb76bdb3d8e53
Source dataset
uspto-grants-1998_03
Patent number
US05731147

Reaction notes

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