Hydrochloric Acid → HCID 15137264, compound

HRID 1653612Notes

Reaction equation

HRID 1653612 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([C:17](OC)=[O:18])[N:14]=[C:13]([C:21](OC)=[O:22])[CH:12]=2)[CH:8]=[C:7]([C:25](OC)=[O:26])[N:6]=1)=O.[BH4-].[Na+].Cl>O1CCOCC1.O>[OH:18][CH2:17][C:15]1[CH:16]=[C:11]([C:9]2[CH:10]=[C:5]([CH2:3][OH:2])[N:6]=[C:7]([CH2:25][OH:26])[CH:8]=2)[CH:12]=[C:13]([CH2:21][OH:22])[N:14]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2762456Tetramethyl [4,4'-bipyridine]-2,2',6,6'-tetracarboxylateHCID 4311764Sodium borohydride

Product 1

HCID 15137264HCID 15137264, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

50 g (128.77 mmol) of 2,2',6,6'-tetra(methoxycarbonyl)-4,4'-bipyridine is dissolved in a mixture of 400 ml of dioxane/400 ml of water and, in portions, 48.71 g (1.28 mol) of sodium borohydride is added thereto. The mixture is stirred overnight at room temperature. The solution is acidified with 5N hydrochloric acid and evaporated to dryness. The residue is suspended in 1 liter of 1N sodium hydroxide solution and extracted three times with 250 ml of chloroform. The organic phases are dried over magnesium sulfate and evaporated under vacuum. The residue is recrystallized from ethanol/ether.

Workup

  1. additionis added
  2. customevaporated to dryness
  3. extractionextracted three times with 250 ml of chloroform
  4. dry with materialThe organic phases are dried over magnesium sulfate
  5. customevaporated under vacuum
  6. customThe residue is recrystallized from ethanol/ether

Sources & evidence

ORD record
ord-c8a1a1d3226444fca592d351c6250c20
Source dataset
uspto-grants-1995_04
Patent number
US05403572

Reaction notes

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