Sodium borohydride → HCID 87319894, compound

HRID 1470958Notes

Reaction equation

HRID 1470958 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([C:12](=[O:26])[CH2:13][CH2:14][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[O:16])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4]>C(O)C>[N+:3]([C:6]1[CH:7]=[C:8]([CH:12]([OH:26])[CH2:13][CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[OH:16])[CH:9]=[CH:10][CH:11]=1)([O-:5])=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 131261401,4-Bis(3-nitrophenyl)butane-1,4-dione

Product 1

HCID 87319894HCID 87319894, compoundYield 103.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.6173 g, 17.74 mmol) was added to a suspension of Example 55A (2.71 g, 8.26 mmol) in ethanol (150 mL) and stirred at ambient temperature for 3 hours. The reaction was quenched with water (˜50 mL) and concentrated to a paste which was taken up in 1:1 MeOH:THF. This suspension was filtered through a celite plug and concentrated. The residue was taken up in toluene and heated with stirring to form a white paste which was then sonicated and scraped until a filterable solid formed. This was filtered, rinsed with toluene and dried under vacuum to afford 2.84 g (100%) of the title compound as an off white solid. MS (DCI) m/z 350 (M+NH4)+.

Workup

  1. customThe reaction was quenched with water (˜50 mL)
  2. concentrationconcentrated to a paste which
  3. filtrationThis suspension was filtered through a celite plug
  4. concentrationconcentrated
  5. temperatureheated
  6. stirringwith stirring
  7. customto form a white paste which
  8. customwas then sonicated
  9. customformed
  10. filtrationThis was filtered
  11. washrinsed with toluene
  12. customdried under vacuum

Sources & evidence

ORD record
ord-bda5aac47dea4ec5b320162d5828417a
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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