Acetic Acid → HCID 59255188, compound

HRID 640263Notes

Reaction equation

HRID 640263 reaction equation
C(O)(=O)C.[CH2:5]([NH:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[N+:21]([O-:23])=[O:22])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[BH4-].[Na+]>CS(C)=O>[CH2:5]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][N+:21]([O-:23])=[O:22])=[CH:15][CH:14]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 59255246HCID 59255246, compound

Product 1

HCID 59255188HCID 59255188, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To an acetic acid (5.8 mL) and dimethyl sulfoxide (100 mL) solution of benzyl-(4-((E)-2-nitro-vinyl)-phenyl)-amine (5.82 g, 22.9 mmol) described in Manufacturing Example 68-1-2 was added sodium borohydride (1.39 g, 36.6 mmol) at room temperature while cooling appropriately. This mixture was stirred for 1 hour at room temperature. The mixture was partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-2:1) to obtain the title compound (2.79 g, 48%).

Workup

  1. temperaturewhile cooling appropriately
  2. customThe mixture was partitioned into ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=4:1-2:1)

Sources & evidence

ORD record
ord-0df0e5a82d0c41db89d514ffa0b63c35
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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